Toy Boy Ch. 02

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Teacher Jenny & ex-student Michael.
3.7k words
4.57
32.3k
14
1

Part 2 of the 6 part series

Updated 09/25/2022
Created 07/24/2013
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Continuing the story of teacher Jenny and her ex-student Michael. Jenny decides on a plan of action, and sets about putting into practice.


Chapter 2 – A First Date?

I found myself inexplicably excited as I got up the next morning. I was looking forward to seeing Michael more than I had expected, and my excitement flowed over into my choices for clothing. I wanted him to like my selections. It was a warm summer day, so I chose a light white cotton sleeveless summer dress with a bold floral print and spaghetti straps, the loose skirt stopping about half-way down my thighs. I briefly debated whether to wear a bra at all or not, but eventually plumped for a white lace strapless one as I hate seeing bra straps, plus matching white lace thong knickers – no V.P.L. for me! Then I chose a pair of white four-inch high stiletto-heel strappy sandals, with ankle straps, to match the base white colour of my dress, and a pair of large gold hoop earrings about four inches in diameter. I took especial care on my makeup, making sure to emphasise my eyes with carefully blended blue and silver eye shadow: lots of sky-blue eyeliner all around my eyes and on the waterline, and then topped off with lots and lots of matching royal-blue mascara to extend my lashes and draw Michael's attention to my eyes. I finished with a pale frosted pink lipstick and matching pink nail polish on my fingers and toes. I left my hair down and loose about my shoulders so the earrings peeked out tantalisingly. I wanted to look at my casual best when Michael picked me up.

"Your carriage awaits." Michael said jokingly as I answered the doorbell, and then he fell silent for a few seconds as he took in my makeup and clothes. I broke his slightly embarrassed pause by quickly busying myself with leaving the house – grabbing my white leather shoulder bag and keys, and then locking the door on my way out. I could see him still admiring me as we walked to his car – a battered old thing that he had clearly washed as best he could. The passenger seat was thankfully clean, no litter in the footwell, and I guessed that he had vacuumed the interior as well. I sat down and then swung my legs in, making sure the skirt of my dress rode high on my legs to show them off. Michael held the door and closed it after me like a true gentleman, and then almost ran around the car to get in the driver's side. We were off.

The drive up was uneventful but enjoyable. The early summer day was warm and his car was old enough to not have air con, which meant it got warmer than was strictly comfortable, but we joked about it happily. We chatted about many things and the time just flew by. One thing I did make sure to do was to subtly slip into the conversation the fact that I did not have a boyfriend at the moment. I wanted to put him at his ease as much as I could, although he did keep surreptitiously glancing at my legs when he thought I wouldn't notice. So I shifted my position in the car seat occasionally in order to tip my knees towards him sensuously, and then back again.

He did seem to relax more in my company as we drove, and started sounding much more at ease in using my name rather than the old formal "Miss". Several times during our conversation I reached out to touch his arm or leg lightly, when laughing at a joke, or as a seemingly natural part of the conversation. I knew now that I wanted to get closer to him, in all senses of the word, but I didn't want to scare him off by moving too fast. The old maxim "Softly, softly catchy monkey" kept playing through my mind.

To avoid the London congestion charge, which we both agreed was a tax-too-far, we parked in the outskirts near a tube station, and made our arrangements for the day. We would meet back here in a few hours this afternoon, and have a small bite to eat at a local café before heading home. Then, just as we were about to part to go our separate ways in the capital, I took his hand in mine for a second and stretched up to give him a quick peck of a kiss on the cheek.

"Thank you for driving me today, it means a lot." I said, and as I walked away I turned briefly and saw him touching his cheek where I had kissed him. He looked so surprised I don't think he knew whether to smile or cry.

* * *

I was nearly half an hour late getting back to the car, and I was carrying enough shopping bags to look like somebody out of the old "Sex and the City" TV series. I had blown my entire clothing budget for the next three months in one go, and it felt great! I was looking forward to wearing everything I had bought, and most of it had been specially selected to be something to get Michael excited. It had been like buying presents for both him and me at the same time. I couldn't wait to see his reaction. Not today though.

Michael was sitting at a small table in the café window and saw me as I hurried along the street, almost trotting on my high-heels. He quickly came to my rescue as I pushed my flustered way through the door, grabbing bags off me before I knocked anything, or anyone, over. Within two minutes I was sitting opposite him, bags arranged neatly around me, and a coffee ordered from the waiter. After a few minutes when I had calmed down, we ordered something light to eat, and I ordered a small glass of wine to go with the meal; Michael had a coke as he was driving – sensible boy!

As we sat and talked over the meal, I couldn't help myself and I kept looking at him through my heavily mascaraed eye lashes over the top of my wine glass. He really was quite handsome in his own way. Tall, and slim as only an eighteen year-old can be, yet with a broadness of shoulder and confidence that belied his years. He moved slightly awkwardly, as if still getting used to his own body as it grew quickly into adulthood. As several lascivious thoughts started to run through my mind I could feel my nipples starting to harden, and even a slight dampness seep into my tiny thong panties, as my body responded to what I was imagining.

As we ate and talked, I did plenty of playing with my hair and looking into his eyes. I hoped he was smart enough to pick up on my deliberate body language, although at his age he might not know enough yet to look for it. Even so, I hoped he might unconsciously pick up on my desire. I also tried to touch his hand or arm across the small table as often as I could without it seeming too out-of-place. Once I even let my foot half-accidentally touch his leg for a second or two longer than was absolutely necessary as I shifted position in my chair.

Michael kept looking at my eyes as we ate, clearly taking in every nuance of how I had done my makeup, and I was glad I had taken such care with it this morning. It was a little subdued now, as the day rushing around London had taken its toll, so while we waited for the bill I took the opportunity to fish my compact mirror from my shoulder-bag, and touch-up the worst of the day's ravages – reapplying my lipstick, and touching up my eye liner. As I did this I was surprised to notice that Michael was squirming in his seat slightly, and trying to look nonchalant. It took me a few seconds to figure out why – watching me doing my makeup had given him an erection! I smiled slightly to myself, and took my time, letting the moment linger as I extended the little ritual more than I actually needed to, adding a flick of blusher with my travel-brush, and a quick touch of extra mascara, even though it wasn't really necessary. I now fully realised that I liked teasing him, and as he tried to hide the bulge in his trousers beneath the tablecloth I just wanted to kiss him all over he was so cute and funny.

Then came the moment. I hoped that Michel was feeling similar to me, as I was about to cross a line from polite friendliness to something more. After we had paid our respective shares of the bill we got up to leave and head back to where his car was parked. As we stood up to leave the restaurant, I deliberately reached out and took Michael's hand in mine, letting my fingers slowly intertwine with his. He glanced down for a second at my hand in his, my pink frosted fingernails and slim fingers contrasting with his. Then he gave my hand a gentle squeeze of reassurance as he looked into my eyes, and I breathed a small sigh of relief. I grabbed half of my many carrier bags with my one free hand, and he grabbed the rest with his free hand, and we walked back to the car in silence, hand-in-hand, lost in our own feelings. Every so often I would glance up to look at him, and several times I caught him looking back down at me – even though I was wearing four-inch heels, he was still several inches taller.

It was only as we busied ourselves with the logistics of loading his small car with all my shopping bags that the conversation started again, a little awkwardly at first, but soon falling back into our now familiar ease. Again he opened the door for me, and I sat down and then slowly swung my legs in letting him have an eyeful as I did so. With my eye-line almost exactly at his crutch level, I could see he had a satisfyingly large bulge in his trousers that I think had been there ever since he had watched me touch-up my makeup in the café. I wanted to reach out and fondle the hard rod of flesh I knew would be beneath that bulge, but I knew it was too soon. We'd only just got as far holding-hands for goodness sake, and I had to consciously restrain myself.

Once we had got going on the return journey, our conversation resumed as easily as it had before. More so if anything in fact, and I found myself telling Michael things about myself that I hadn't told anyone before. He found out about my double-life, and I even admitted to noticing how he had used to look at me in class. He had blushed slightly at this, but since we had moved on in our burgeoning relationship slightly, he took it in his stride, and admitted that he'd had a little crush on me ever since those early days at school, trying to make light of it by making it into a little joke. It was all perfectly natural for boys to get schoolboy crushes at school I reassured him; and here I must admit to a small white lie as I told him that, at the time, it hadn't mattered to me and that I hadn't thought much of it. He politely tried to ask about my shopping trip, I guess he was hoping to get some clues as to what I'd bought, but I kept my answers deliberately vague under the excuse that a man wouldn't be interested in girl-clothes, and he thankfully left it at that. I wanted the results of my decadent spending-spree to be a surprise after all.

As the miles slipped by, Michael seemed to relax into talking more about feelings and emotions in general, slowly opening up his heart to me. When we arrived at my door, the journey had seemed to pass all too quickly, and I was desperately trying to think of another excuse to see him again.

Michael helped me carry all my various shopping bags indoors, and then I walked with him back to the front door. As he turned to say goodbye I looked up straight into his eyes with a smile, and then I reached up to put a hand behind his neck, whilst holding his other hand in my own. He gently resisted for a second until he realised what I was doing, then I slowly pulled his head down to mine, and kissed him on the lips. I was almost quivering I was so excited, and I held the kiss for just a few seconds - no tongues - but long enough to hopefully let him know that it was more than just mere politeness. I had really crossed the line now, but I was still wracking my brains to think of an excuse to see him again.

"Thank you so much again for driving me." I said as huskily our lips parted. "I had a lovely day."

"So did I," he replied, and then I could see him actually brace himself as he asked the big question, "could I see you again?" The look on his face was almost comical as he waited to see if his advances would be rejected yet again – just like he had always been before with the girls at school. I decided to put him out of his misery quickly. I wasn't going to play games with him.

"Yes, I'd like that very much." I said, following up with the question that would mean I didn't have to wrack my brains for any more lame excuses, "Did you have anything in mind?"

I think I must have caught him slightly off-guard with my question, as he suddenly paused.

"Ah. Erm. Well, I, erm, was planning to go swimming the day after tomorrow, but I wasn't sure if you'd like that or not...?" He trailed off. I thought about it for a few seconds and decided that actually I quite liked the idea.

"Swimming? Sure! I haven't been swimming forages. That sounds like a fun thing to do. Do you want to meet at the leisure centre? I expect to pick my car up from the garage that morning, so I'll be mobile again."

Michael's broad smile said it all, and we arranged a time. Then I reached up to put my hand behind his neck and pulled him down to kiss him briefly again. He relaxed into it more after I had caught him slightly by surprise last time, and we kissed for a very tiny bit longer. I still kept it fairly chaste – no tongues again – and I could feel him gently pulling his abdomen away from my stomach as he didn't want his aroused state to be too obvious. I smiled inwardly to myself, and again had to consciously restrain myself from reaching out to fondle his erect cock.

Our lips parted, and as he pulled away to go, his hand came up and he gently caressed my cheek with his fingertips in the very softest of touches. At that moment my heart just absolutely melted. I went slightly weak at the knees, and I knew that from this moment onwards I was his. I couldn't help myself, and I quickly planted the tiniest peck of a kiss on his lips as a parting gesture; like a little signature.

"See you soon." I said. "I can't wait!" Where had that come from? I blushed at what I had just said, but he pretended not to notice my sudden embarrassment.

"Bye, Jenny." Was all he said, and with that, he headed off back down the path to his car. I closed my front door behind him, and leaned hard against it, aghast at what had blurted just out of my mouth. As I calmed down, I took a grip of myself, and went to unpack my day's shopping.

* * *

A little later, looking at what I had bought as it lay spread out on my bed, I started to get excited all over again. I had been especially brazen in my purchases, and the thought of wearing such overtly sexy items in public made me blush at my own daring, and yet thrilled me at the same time. I could feel my body responding already with excitement at the thought, but thankfully now I was alone and in a position to do something about it.

I quickly tidied up my day's shopping and slipped out of my dress. Leaving my high-heeled shoes and underwear on, I lay down on the bed and reached over to my bedside cabinet. Opening the drawer, I pulled out my large "rabbit" style vibrator. I knew I wanted Michael badly, but he wasn't here, so this was my next best thing. It was a good seven inches long, and so thick that I could hardly get my hand around it. Made of a flexible semi-translucent plastic material, inside were dozens of pearl-like spheres that bulged through the sides, and from the base came a long finger-like appendage that ended in two small flexible prongs – the "rabbit ears".

I ran my hands over my body, and could feel my nipples already hard through the material of my bra. I pinched them hard, tingling as the feelings coursed through my body. I could feel my thong knickers were damp, and I reached one hand down to slip beneath the elastic to my throbbing pussy. It was hot, and my juices were flowing freely now, making my fingers slick as I slowly rubbed myself.

I rubbed from my clitoris down to my pussy entrance, which was slick and wet, slipping a finger inside for a couple of delicious seconds before working back up to my clit again. Back and forth, back and forth. I was writhing on the bed, with one hand now buried in my crotch and the thick vibrator held in my other hand. When I felt I wanted more I pulled my knickers to one side and pushed the thick round end of the vibrator against my quivering entrance. Gradually I eased it into me, thrusting very slowly in and out, pushing in just a fraction further each time as my juices flowed to lubricate the passage. I could feel it stretching me open, filling me up. It was a very tight fit, and I loved the feeling of being stretched that it gave.

I was already panting hard as my excitement mounted further. I could imagine Michael pushing his cock into me as I held him in my arms, his body weight pressing me down into the mattress as we kissed deeply. As I slowly pushed the thick rod in to about three quarters of its length, I pressed the first button, and a wave of pleasure passed up my body as the beads inside started to rotate, pulsing and rippling against the sensitive entrance to my pussy. I couldn't wait any more, I was writhing and panting in ecstasy. With a single thrust I pushed the vibrator hard up inside me as far as it could go, feeling it stretch me wide open all the way up. At the same time, I felt the two "rabbit ears" come up against my clit. I gasped and panted with expectant pleasure, and knowing exactly what would happen, I pressed the second button.

I almost screamed as the two flexible rabbit ears started to vibrate rapidly against my clit. Waves of pleasure rolled up and down my entire body as I repeatedly thrust the vibrator deep into my pussy and then pulled it out again. It could feel my vagina walls stretched absolutely tight around it so that it almost felt like it was splitting me open with each thrust. Each time I got to the top of a thrust, the vibrating rabbit ears would embrace my clitoris and I would feel myself get closer and closer to a climax. I wanted to prolong this as long as possible, so I would then pull it out until just the round head was inside me, holding it there for a few seconds before thrusting deeply back in, feeling the vibrating impact of the rabbit ears against my clitoris and the stretching of my pussy walls afresh each time.

I kept this rhythm going for as long as I could stand to hold back, until I could resist no longer. I thrust the vibrator hard up inside myself as far as it would go one last time. It stretched me wide, with the rotating beads rippling against the sensitive flesh of my pussy-entrance and the swiftly vibrating rabbit ears hard against my clitoris. This time I held it there. With my clitoris being stimulated by the rapid vibrations it didn't take long before a massive orgasm rolled through my body in waves. As I came I couldn't help myself, and I screamed out loud, my whole body tingling and throbbing. I held the vibrator inside me for as long as I could stand it, coming over and over again, my pussy tightening spasmodically against the rippling beads as they continued to stimulate my sensitive labia lips.

Just when I thought I would pass out, I slowly pulled the vibrator from my quivering body, and switched it off. As the noise of it ceased, I lay there panting and trembling as I came down from the ecstasy-high. I wanted Michael so badly at that moment that I almost phoned him up to ask him back to my house there and then. The only thing that stopped me was the knowledge that I wanted his first time to be special for him too. And I also wanted an opportunity to show off some of my new purchases.

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1 Comments
GalilaoGalilaoover 10 years ago
Amazing story so far!

amazing story so far, can't wait to read the next chapter. the slow yet intense build up is great. hope chapter 3 is as good or better than the first 2!

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Toy Boy Series Info

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