The Teacher

Story Info
A second date turns in to a long night.
1.9k words
4.05
48.8k
7
2
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

After dating the accountant for about 6 weeks she began to talk about moving in together, marriage and kids. Having just come out of an 18 year marriage I was not keen on this enthusiasm and so the relationship petered out.

It wasn't too long however before I got bored being on my own and decided to start dating again.

My next girl friend was a school teacher who had been married but was now separated and had been for some five years during which time she had hardly dated at all but concentrated on brining up her son who was now 8 years old.

Cathy was 35, a little younger than me, but stood at just about 5 feet 1 inch tall, some 7 inches shorter than my 5 foot 8 inches. She had long dark hair that tumbled down to her shoulders in natural curls that made it look almost permed. Though English her facial features looked almost Spanish, helped of course by her hair, though her skin was not tanned like someone from the Mediterranean.

She was not slim but carried no extra weight and despite her shortness she was well proportioned with small breasts, nice hips and rounded, pert bottom.

Our first date was in a pub and I nearly blew things when I was so shy that I could barely look Cathy in the eye and it was a struggle to kiss her good bye when the date ended.

I was surprised to get a second date a week later and we met in the same pub where she told me her son was stopping out for the night at his grandparents so I could go back to her house if I liked for a coffee.

I agreed and she drove us to a detached house on a quiet housing development.

The idea of coffee went out the window and we shared a bottle of wine instead. As time ticked on Cathy said I could stay the night if I liked and have the guest bedroom.

I thought this was a good idea as it saved me a trip home on the late night train. I was note prepared in that I didn't have an over-night bag but thought I could manage for one night.

I stripped down to my shorts and was soon in bed with the light out, listening to here if Cathy was also going to bed in the room next door. The wine had gone to my head a little more than I expected and I was struggling to stay awake. I was laid with my back to the door and started to drift in to sleep when I felt the duvet lift and Cathy climbing in to bed next to me.

I turned and we immediately began kissing. Her warm body was naked and I could feel her breasts on my chest as I pulled her close. As we continued to kiss I let my hands slip down Cathy's sides until they rested on her firm arse which I stroked.

Suddenly Cathy put her palms on my chest I could feel her wriggling down my body as she push me on to my back. Her hands took hold of the top of my shorts and slid them down, freeing my erect penis which she immediately grabbed and slowly but firmly she forced back my foreskin to expose the throbbing head.

She took me in to her mouth and began to work her tongue slowly all over my knob. The sensation was fantastic and I had to pinch myself to remember this was only my second date with this woman.

As she licked around the top of my shaft she began to slowly move her hand up and down my cock, wanking me gently in to her mouth.

I felt almost guilty as my pleasure built as I could not reach any part of Cathy's body to reciprocate and just paid back and enjoyed waves of pleasure flowing from my groin.

My excitement was growing and Cathy must have noticed the small twitches my dick was now making and instead of stopping she began wanking me faster and harder, sucking me deeper in to her mouth as she did this.

I closed my eyes and grasped the bed sheet, trying to fight off the inevitable, but it was impossible and my body suddenly went rigid as my dick twitched one last time and hot spunk came out in spurts in to Cathy's mouth.

Cathy left the bed and I could do no more than lay there and soon fell in to a light sleep, sensing Cathy returning to the bed and snuggling up to me shortly after.

It was difficult for me to say how long I dosed for, but I awoke with a semi-erection as I need the toilet. I gently left the bed trying not to disturb Cathy. When I returned I got back under the duvet she started kissing my neck and I instinctively reached out and felt her breast, squeezing each before gently working her nipples in to stiff little pointers.

I was erect again by this time and rolled on to my back, easing Cathy on top of me so our groins me. She could feel my cock pressing her bell as I began to suck each breast in turn, flicking my tongue quickly across each nipple before closing my teeth and tugging gently.

Starting to emit little moans, Cathy felt down and guided my erection in to her vagina. I moved my own hand down to help her and could feel that she had no pubic hair, a fact I had not appreciated as we had both been under the duvet in the dark and I had not had the opportunity to nuzzle her cunt yet.

With cock in now Cathy began to slowly ride up and down on my shaft, her pussy feeling quite tight. She transferred her weight a little further back as her rhythm began to increase and was soon bouncing up and down quite happily, the duvet having been discarded from the bed.

At first I lay as still as possible and left the work to Cathy, but as her rhythm increased I couldn't help but start to push myself upwards from the bed to meet her downwards thrusts. Up and down she went and in the darkness I could just make out the outline of her tits moving up and down in harmony with the rest of her body, though only slightly as a result of their modest size.

I focussed hard to stop myself coming and this paid off as before long I felt Cathy thrusting down harder, her breath coming in ragged gasps before she suddenly pushed herself on to my cock really hard but didn't ride back up it this time as her legs gripped tightly around my thighs and her orgasm came.

After a few seconds I could feel her relax and she suggested we change positions. She slowly raised herself up and lifted herself off my cock.

I began to move but let out a gasp of pain as something in my lower back pulled.

Cathy asked me what was wrong and I explained it was just old age. She immediately suggested I might benefit from a little massage and reached over to her bedside dresser. She opened the top drawer and rummaged in the dark for a little while then closed the drawer again.

She then told me to lay on my front and she poured some oil on to my lower back from a small bottle she had taken from the dresser.

Carefully and gently she began to rub my back and the sensation quickly eased my discomfort and relaxed me. I sank in to the mattress and she worked away, a little firmer now, making me feel so damn good.

Not wanting to hog all the pleasure I told Cathy I would give her back a rub, wanting to show off a skill I had acquired with the accountant who really liked a massage as a pre-curser to sex.

Cathy agreed and rolled on to her stomach, handing me the small bottle.

I put a little oil on my hands and dribbled a little down the length of her spine then went to work gently kneading and massaging, working my way from Cathy's shoulders to her arse and back up again.

As I worked my way down again Cathy lifted her midriff from the bed and was stroking herself between the legs as I worked.

Early morning light was growing outside and though it was still quite dark in the bedroom I could start to make out a little more detail, the colour of flesh now more apparent than it was in the pitch blackness of the night.

I stopped the massage and watched as Cathy continued to stroke herself. As the light increased a little more I could just about make out her fingers penetrating her pussy.

She now lifted up a little higher, resting on one arm she rubbed herself harder and pushed her arse in the air. I had the perfect view of her masturbating.

As she continued rubbing she ask me for the oil. She stopped pleasuring herself for a second, kneeled upright, poured some oil on to her right hand then bent forward again leaning on her left arm with her face almost in the pillow and her arse again stuck high in the air.

Again her fingers came between her legs but this time didn't stop at her pussy but move on to her anus. She rubbed gently across the opening, allowing the oil on her fingers to moisten the little tight hole.

My erection was growing harder at this show and soon her ring and forefingers were disappearing up to the middle joints as they pushed in to her now lubricated arse hole.

Sticking her bottom higher in the air Cathy suddenly told me to stick my cock in her arse. I was shocked, having only ever tried anal sex once and not expecting this on a second date.

She removed her fingers which went to work on her pussy as I eased towards her so that the head of my penis just touched her anal passage opening.

I pulled back my foreskin and pushed, feeling some resistance as my knob began to disappear in to Cathy's arse. Just a little way in I paused, worried this might be uncomfortable for her. In answer she pushed herself backwards so her hole swallowed up three quarters of my shaft.

I then very gently pulled back and then gently thrust forward again, my movements measured and careful.

Cathy began to rub her bare pussy lips more frantically and as I pushed in to her she moved back harder on to my cock with each thrust.

I closed my eyes and stopped thrusting as I felt very close to shooting my load. I told Cathy I was about to come and she responded by speeding up her own movements so that she slid up and down on my hard cock which was gripped in her tight little arse.

It was impossible to resist the urge and as I she pushed back on to my prick harder than ever I couldn't stop myself exploding in to her. When the twitching stopped Cathy pulled forwards until my cock came out of her arse and she then laid on her back, legs open and rubbed herself hard until she reached orgasm a few minutes later.

We both slept soundly after that and I dreamt of what might happen on our third date.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
knickerlessalwaysknickerlessalwaysover 15 years ago
Has she any colleagues?

Ask your teacher friend if she has any male colleagues of a similar disposition, please.

skip.69skip.69over 15 years ago
Roll on

Roll on your thrid date - and the fourth and fifth and so ad finitum!

Share this Story

Similar Stories

Bagging Lauren A teenager fucks his third middle-aged woman in six months.in Mature
Amanda's Path to Discovery Pt. 01 A frustrated wife sets out to find company.in Interracial Love
My Wife's Accidental Affair Account of the accidental beginning of an affair.in Loving Wives
Tight Jeans A church-going wife learns to love attracting men.in Loving Wives
Owned A happily married mother is owned by well hung black man.in Fetish
More Stories