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My Old Student

A chance meeting with an old student leads to an unusual proposition.
I was returning to the car from the cashpoint when a voice came out of the darkness, “Hey, honey. Looking for business?”

I turned around, the refusal on my lips dying as I looked at the girl in front of me.

“Rosie?” I asked, shocked, “What are you doing here? I thought you were at university?”

“Mr. Grey! Oh God! It’s not what it looks like, honest!” exclaimed the girl, her shocked expression mirroring my own.

I had been Rosie’s form tutor some years previously when she was about in senior high. I remembered her as a shy and slightly gawky girl but nevertheless intelligent and hard working. If anyone had told me that one of my pupils was going to become a working girl I wouldn’t, in a million years, have suspected Rosie.

There was no doubt that she had changed though.

From a rather plain chubby girl she had become a beautiful woman; petite and slim with long wavy blond hair. She was wearing a cropped low cut tee-shirt which revealed both her toned stomach, complete with belly button ring, and the twin mounds of her breasts. Her miniskirt and holdups were perfectly placed to flash a strip of flesh as she walked and showed off her long slim legs to great effect. The outfit was completed by a pair of strappy high heeled shoes and a small handbag slung from one shoulder.

I have never felt the slightest hint of sexual desire for any of my students. Even when I met them years later, no matter how old they were, they remained ‘my pupils’ and I tended to view them with a certain paternal air.

Looking at Rosie now, however, I felt a stirring of desire.

“Well, it looks like you’ve become a hooker, to be honest.” I said sternly.

Rosie stood there with her hands clasped in front of her and her head down so that her hair swung forward to cover her face. Suddenly I was reminded of the shy school girl who used to stand before me all those years ago and I felt ashamed that I had even now thought about her in a sexual way.

I relented of my earlier harshness and spoke more gently, “But, obviously, you are not a prostitute. So what is going on?”

“It’s a game, sir.” She replied meekly.

“A game?” I echoed.

Rosie nodded, “My boyfriend and I had been watching that Secret Diary of a Call Girl on TV and I kind of said... ...I kind of wondered what it’s like to be a call girl and he, that’s my boyfriend, he got really excited by the idea. So I kind of said I would pretend to be one for him.”

“So, you stand here pretending to be on the game and he pretends to pick you up?” I asked.

“Err.. ..no, not really.” She replied awkwardly.

“We agreed I’d pick someone up. My boyfriend would follow us in his car then wait while I err, well you know, while I ‘do it’, and then he’d pick me up afterwards and I’d tell him all about it.”

“Oh, Rosie! That sounds extremely dangerous. I mean, anything could happen to you. You could get stopped by the police or picked up by some complete weirdo. And anyway,” I continued as a new objection occurred to me, ”If you’re taking money for sex, what’s the difference between playing at being a prostitute and actually being one?”

Rosie looked shocked, “Oh, I wasn’t actually going to take money from anyone! I was going to explain what was going on, that it’s just a fantasy.”

To me it sounded like the boundary between fantasy and reality could get dangerously blurred if she wasn’t careful. I wracked my brains to think of some way to dissuade her.

In the absence of anything else I said, “Okay, so your boyfriend likes the idea of you pretending to be a call girl, but how do you feel about it?”

Rosie frowned then sighed, “It was a real turn on at the start, you know, planning it and getting ready and stuff, but I’ve been hanging around for ages and, well, to be honest, when blokes have stopped I’ve been too scared to go through with it.”

“So tell your boyfriend that.” I suggested.

Rosie looked pensive, “I don’t think I could. He’s really excited by the idea and I don’t want to let him down.”

I must confess, it sounded to me like she had got herself into an abusive relationship but I wasn’t sure how to say that without putting Rosie on the defensive.

“So, how old’s your boyfriend?” I asked eventually.

“What? Lee? He’s the year above me at Uni so he’d be nineteen.” She replied.

I sighed, “Look, do you want me to have a word with him? I mean, if you think it would help.”

I knew I was grasping at straws but I didn’t want to just leave her there.

Rosie shook her head, “No, no, you’re okay, thanks.”

“Okay then, I’d better go. See you, Rosie. Look after yourself.”

I turned away sadly. Part of me thought it wasn’t my problem, she was a grown woman who could make her own choices, but part of me still remembered her as the shy little schoolgirl and I knew I wouldn’t forgive myself if anything happened to her.

“Actually, sir.” Rosie called after me, “There is something you could do.”

“What’s that?” I asked turning back to her.

A cheeky grin appeared on her face and she struck what I imagine she thought of as a seductive pose, ”You could offer a girl some business!”

I wasn’t sure whether to laugh or be shocked. I wanted to tell her that there were a hundred reasons why it wasn’t a good idea but, as I thought about it, I realised that there weren’t that many reasons.

She was no longer a student of mine but an attractive young woman, and the fact that she had been my pupil gave a certain frisson to the idea.

Eventually I nodded with a show of reluctance that hid the growing excitement within me. Of course, I told myself, I’m getting her off the streets and somewhere safe, but I knew that was no longer my main concern.

We walked to the car and got in. As we put on our seat belts Rosie turned to me, “Listen. Could you drive past the car park round the corner, just so my boyfriend knows to follow. I’ll just text him.”

She pulled out a mobile phone from her handbag and the screen lit up. She quickly tapped a message on the keyboard then, without waiting for a reply, turned it off and slid it back into her bag and placed it on the dashboard.

I noted that there was a single vehicle in the car park. As we passed, its headlights came on and it slowly moved off, taking up station behind us. My heart was in my mouth but if Rosie was nervous she didn’t show it unless it was in the constant chatter about her life at Uni.

We drove for a while with Rosie occasionally giving directions, the headlights of her boyfriend’s car in my rear view mirror, until we entered the local industrial estate. Finally Rosie told me to turn into a layby and stop the car. The other car stopped behind us and the headlights went off.

We were next to some sort of storage depot and the floodlights lit the whole area so I could see Rosie clearly in their glare.

“Are you sure we’re safe.” I asked, feeling exposed in the bright light.

“Yeah, no problem.” She replied, removing her seat belt, “Lee and I sometimes come here for a quickie when I’m home from Uni. It’d be nice to use the house but there’s no way my mum would let us.”

I undid my own seat belt and turned the overhead dome light on, then we turned to face each other.

“What now?” I whispered.

“Well,” She said coyly, “we could start like this...”

She lent forward and kissed me. At first it was just a light brush of her lips against my own, then I felt Rosie press harder and the tip of her tongue darted into my mouth. The fingers of her hand lightly traced a pattern up the inside leg of my trousers. Suddenly she broke away.

“Oh, I just remembered!” She laughed, “Prostitutes aren’t supposed to kiss their clients are they?”

“That’s a pity,” I replied, “I was enjoying that.”

“Mm, okay then...” and we returned to the kiss. Her hand wandered higher up my leg until she was caressing my groin.

I placed my hand on her bare midriff and let it wander upwards until, with an almost electric shock, it came into contact with the swell of her breast and I felt my cock give a little twitch. I let my hand wander until I could hold the soft globe in my hand, my thumb making circular motions around the harder flesh of her nipple.

“Listen, can we push these seats back a bit?” Rosie asked, breaking from the kiss and sitting back.

I showed her were the controls were and we both pushed out seats back as far as they could go and reclined them until we had plenty of room.

Rosie quickly stripped off her tee-shirt to reveal that she was without a bra, then knelt on the passenger seat facing me. She folded her arms underneath her boobs and gave a little jiggle so that her breasts bounced seductively.

“Like them?” She asked with a grin.

“Oh yes!” I replied enthusiastically, “I just want them... here!”

I reached out my arm meaning to pull her in close so I could suck on her tits but Rosie pulled back.

“Uh, uh, trousers off first!” she ordered.

I quickly undid the button and zip and pushed my trousers and pants down until they slipped round my ankles, then I reached for her again. This time she didn’t resist but bent forward, wrapping one arm around my neck, so that I could would have easy access to her breasts.

I took her nipple in my mouth, playing with it with my lips and tongue. My hand massaging her other breast, gently rolling the nipple between my finger and thumb.

Rosie gave a sigh and her hand strayed to my cock. She started to move her fingers up and down my shaft, lightly at first so that she was just caressing the skin, then harder until her hand was gripping me firmly.

At last she seemed satisfied that I was completely erect and, removing her arm from around my neck, she bent forward over my cock. At the same time she reached behind herself, hitched up the hem of her miniskirt and gathered the material about her waist to reveal the twin moons of her ass glowing in the light of the storage depot.

Her hair fell forward so I couldn’t see what was going on but I felt the heat of her mouth as she wrapped her lips around my erection and I gave an involuntary groan at the sensation. With one hand I brushed her hair to one side and held it there so I could watch as she slowly rocked her head backwards and forwards, her lips and tongue moving up and down the shaft of my cock.

I trailed my fingers down her spine and over the gathered material of her miniskirt, briefly caressing the cool flesh of her buttocks before following the curve of her ass round towards her pussy.

l parted the opening to her cunt and felt the heat of her arousal. She was incredibly wet but still tight, and I struggled to slip even one of my finger inside her. Rather than force it, I stretched further round and Rosie gave a muffled squeak as my index finger, already lubricated with her juices, found the little flap of skin and pushed the hard button inside.

“Is that okay?” I whispered.

Without breaking off from what she was doing, Rosie nodded and mumbled what I took to be assent, so I continued to lightly rub Rosie’s clit. Her breathing became faster and she began to move her hips, forcing my finger to press more firmly on her little nub of flesh.

After a few minutes she lifted her head and gasped, “Please sir! Put your fingers inside me.”

I moved my hand and gently massaged the opening of her pussy until I was able to get the tips of first one, then two, fingers inside her. I still marvelled at how hot she was, and how tight, despite the juices that covered my fingers.

Rosie began to shudder and moan as my finger tips explored her cunt. She shuffled in her seat, arching her back so I could push my fingers further inside. She withdrew her mouth from my cock and, wrapping her fingers around the shaft, started to wank me with short quick movements. I pushed my fingers in and out of her, my rhythm unconsciously matching the rhythm of Rosie’s hand.

I could feel myself approaching climax, spurred on not only by Rosie’s fingers on my prick but by the little spasms and jerks her body was giving and the low groans that were emerging from her lips. I knew I couldn’t last long.

“Oh fuck! I’m cumming!” I muttered.

Without slackening the pace of her hand, Rosie quickly wrapped her lips around the head of my cock as I began to ejaculate. The sensation of cumming into her warm mouth seemed to go on forever and I became aware that I was panting hard.

Just then Rosie gave a series of incoherent cries and the walls of her cunt contract tightly, almost painfully, around my fingers as her own orgasm rode her. She still had her mouth and fingers around my cock, and for a moment she went very still. Then her hand tightened, and she began moving it slowly up and down as if she was determined to squeeze every last drop of spunk into her mouth.

I still had my fingers inside her and, as I started to withdraw them, Rosie gave a low moan.

She pulled her mouth away from my cock and sat back on her haunches, her lips clamped together, her mouth a thin line. Slowly she opened her mouth and, in the glow of the dome light, I could see her tongue coated with a mixture of cum and saliva.

Rosie grinned, then turned to the car door. Opening it, she spat, then spat again. After a minute she turned back and reached for her handbag.

“Sorry about that.” She said, pulling a tissue from her bag and wiping her mouth with it, “I love having men cum in my mouth but I can’t stand the thought of swallowing it. Here do you want one?”

She handed me a tissue and I began cleaning myself up before pulling my trousers up. While Rosie was busy performing a similar task I grabbed a pen and paper and quickly wrote down my number. As she was straightening her clothes I turned to her:

“Rosie, will you do me a favour?”

She nodded, “Sure, what is it?”

“Well, I know I have no right to ask, I don’t want you to do this again.” I appealed.

Rosie looked perplexed then hurt, “Didn’t you enjoy it?”

“I don’t mean this, this was great.” I paused to gather my thoughts then carried on, ”What I mean is, I don’t want you pretending to be a prostitute again.”

“Oh!” She frowned then gave a vague smile, “Okay.”

I could tell she didn’t mean it and maybe didn’t even see what the problem was but I was still worried about her.

“Look, here’s my number just in case you want a chat.” I handed her the piece of paper.

“Just a chat?” She asked coyly.

I just raised my eyebrows and gave her a hard stare.

Rosie giggled, ”You know, when you used to look at us like that in class we were all very frightened of you.”

“That was the effect I was going for.” I grinned.

Rosie smiled and took the piece of paper before giving me a brief peck on the cheek, “Thanks Mr. Grey, you were always my favourite teacher.”

I watched as Rosie got out of the car and made her way towards where her boyfriend was parked and I reflected on what a strange evening it had been. I was genuinely concerned about her and I hoped Rosie would call.

However, I knew she was right, it wouldn’t just be for a chat.

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