Straight Male / 43
Jess Part One.
Disclaimer. The events may be true, or they are just a fragment of my imagination that is for the reader to decide. To protect the innocent, or the guilty, I have taken the liberty of using random names solely for the purpose of this confession. The names of villages and towns are real, and it is just co-incidence if person(s) of that name live in that village or town. I have presented this as things happened and from memories as I recall them.
This was about 5 years ago and was a driving instructor working for a well-known national driving school. I had taken over some work from an instructor who had retired and meant working outside my immediate area. This story starts from a simple word that was misunderstood and led to eventual unexpected fun.
Dorking and the surrounding Villages and towns are ripe with expensive houses and upper-class persons, TV personalities, footballers, and ordinary people. I was impressed and felt out of place driving through the Village of Box Hill seeing the multi-million-pound houses and array of high-performance cars and even a couple of limousines.
I felt self-conscious, here I was in my trousers and t-shirt when a shirt and tie would be more appropriate, but at least I could slip on my fleece with the company logo on. Not knowing the area, I had given myself plenty of time and arrived in good time. I stopped briefly to check the address and noted I was there. It was a mid-sized house next to a small village shop with a short in and out drive. I parked outside and exited my car. I had time for a smoke.
I saw a little group of people walking towards me, one looked familiar. She was a pale faced redhead. She was in her late teens. I studied her as the group got nearer, she was of average build for her 5 feet 5 height, and her light copper hair suited her attractive looks. I noted her light thin freckles and our eyes met. I found myself grinning at her. She smiled and raised her eyebrows at me obviously pleased I was admiring her. I inspected her as the group passed and walked out of view.
I knew that face, but I had never been here before and I could not place where I seen her. You never forget a pretty girl and she was a redhead, a favourite of mine. I was sure it would come to me but for now, it was time for work.
Jess was in her early to middle twenties. She was of average build for her five-foot six frame, she was not stunningly attractive nor ugly, just an average young lady who displayed shyness and innocence that took me by surprise when we first met. She was wearing smart jacket, blouse and trousers that was her banking assistant uniform. Her long hair was all tied up in a beehive style and she wore make up that did nothing for her looks.
She had had plenty of lessons as a teenager, had been close to driving test standard but had stopped, due to a family problem and only recently taken driving up again. Despite that she was a good driver and very competent. She did not say much, and it was left to me to make conservation as we got to know each other better over the weeks.
Over the weeks I learned Jess was engaged, he had been her only boyfriend and was a technician in the RAF and currently away for a few months in the Falklands. I told her I was married for the second time and had three children. The house was her parents and her nan lived there too.
It was always a rush for her she confessed, literally she got off the bus from work and straight into the driving seat. Could she have a later lesson. Her last instructor would not change things for her. It would mean finishing later than I wanted but agreed to change her lesson to a later evening slot that suited her.
The following week, I pulled onto the drive. A few moments later Jess came out with the redhead I had seen before. The redhead eyed me as she passed and flirty smiles were exchanged as she walked out onto the road. I was surprised at Jess’s plainness. She was wearing a tatty pair of jeans and similar jacket over a plain dark t-shirt. Her long dark blonde hair was loose, and she was not wearing any make up. She looked completely different and plain and that for some reason excited me. She looked sexually appealing and turned me on rapidly.
Jess commented on my expression and strange looks I was giving her. I told her she looked good and had surprised me with her attractive looks. She said something about me just saying that, but I took a risk and without thinking told her she looked so good it had aroused me. She took the briefest of looks and checked out the bulge in my trousers then smiled with a little embarrassment.
I thought I had offended her as she was unusually quiet and said nothing as we went round on the first hour of our two-hour session. I found the courage to bring the subject up and apologised for being out of order.
Jess laughed saying she was not offended but flattered she had made me like that and confirmed she was no prude, then added my bulge looked rather impressive. She changed the subject and we continued going round the circuit. We headed back towards Dorking, but there was something I needed to her to catch up on and told her to come off the A24 by-pass and pull into the bikers’ café.
I took the opportunity to get her to do some reversing and bay parks then told her to park up. I told her to relax and remove her seat belt so that we could do some oral. It was the wrong way to put it. Jess looked at me a little shocked. I beg your pardon she said, that’s inappropriate, and told me she and I were spoken for and asked what I was playing at suggesting such things.
I must confess I laughed when I realised what I had said. She did not find it funny at all until I explained I meant we should do some Q & A for her up and coming test in a couple of weeks. She laughed at her own mistake. I then told her I would love to give her oral if she wanted. She looked at me and inquisitively asked did I say I would give her oral.
I told her yes and added I would treat her to my bare married cock and not pull out of her either. Her face was one of surprised shock. I was certain I caught a hint of aroused pussy as she playfully slapped me in the arm saying that was crude and naughty. The lesson recommenced with me asking the Questions and correcting her on some answers.
We got back to her house and Jess told me she was busy the following week and not sure about the week after as she thought she would be away on a work course. Her driving test was a few weeks or so after that. She would phone the office to book another lesson when she returned. I had obviously gone too far. She would make a complaint and probably get another school to take her for her test. Damn.
I waited to be called into the office about my conduct, a day passed, then a week, but nothing. It had been three weeks and I had forgotten about Jess. Then the office phoned telling me she had booked a two-hour lesson for the Sunday evening. I had mixed feelings as I pulled up her on her drive and waited. She came out looking rather stunning I must say, she had put her hair into plaits and wearing simple flowing lacy top and loose-fitting trousers.
My cock was solid as she slipped into the driver’s seat. I complimented her on her hair style. Her eyes scanned my bulge and she had a little grin as she checked out my bulge making it obvious, but I kept it professional and made a start on the lesson plans.
Her driving was not at her usual standard, she had something on her mind. As we drove, I asked if everything was okay. She told me she had not had sex for ages and wondered if I would give her oral, just oral in the car and she would jerk me off. I told her to drive somewhere quiet if she wanted to find out. Jess looked uncertain.
I was not certain either, it was just a hopeful comment with the expectation that it would go no further. We were close to Chessington theme park. She pulled in and parked up in a corner face in. She became extremely nervous. She was shaking slightly as she looked at me. She composed herself and then crudely asked if I was teasing her or going to eat her c**t out.
My car was a sort of smaller version of an MPV, Jess unzipped her trousers and sat on the middle rear seat with the seats set back slightly. She did not want any kissing and told me what I could and could not do to her. I sat next to her right side but to the side exploring her breasts through her top with my right hand. She was not wearing a bra. Her breasts were a fair size and I wanted to suck them but that was not allowed.
I slipped my left hand down and pushed my hand inside her knickers and felt her trimmed pussy hair. I spent a moment rubbing through her mound intently and teased over her lips. I pushed a finger in-between her damp lips and explored her wetting inners adding a second finger and found her clit and strummed on it with a thumb fingering her at the same time.
This was about 5 years ago and was a driving instructor working for a well-known national driving school. I had taken over some work from an instructor who had retired and meant working outside my immediate area. This story starts from a simple word that was misunderstood and led to eventual unexpected fun.
Dorking and the surrounding Villages and towns are ripe with expensive houses and upper-class persons, TV personalities, footballers, and ordinary people. I was impressed and felt out of place driving through the Village of Box Hill seeing the multi-million-pound houses and array of high-performance cars and even a couple of limousines.
I felt self-conscious, here I was in my trousers and t-shirt when a shirt and tie would be more appropriate, but at least I could slip on my fleece with the company logo on. Not knowing the area, I had given myself plenty of time and arrived in good time. I stopped briefly to check the address and noted I was there. It was a mid-sized house next to a small village shop with a short in and out drive. I parked outside and exited my car. I had time for a smoke.
I saw a little group of people walking towards me, one looked familiar. She was a pale faced redhead. She was in her late teens. I studied her as the group got nearer, she was of average build for her 5 feet 5 height, and her light copper hair suited her attractive looks. I noted her light thin freckles and our eyes met. I found myself grinning at her. She smiled and raised her eyebrows at me obviously pleased I was admiring her. I inspected her as the group passed and walked out of view.
I knew that face, but I had never been here before and I could not place where I seen her. You never forget a pretty girl and she was a redhead, a favourite of mine. I was sure it would come to me but for now, it was time for work.
Jess was in her early to middle twenties. She was of average build for her five-foot six frame, she was not stunningly attractive nor ugly, just an average young lady who displayed shyness and innocence that took me by surprise when we first met. She was wearing smart jacket, blouse and trousers that was her banking assistant uniform. Her long hair was all tied up in a beehive style and she wore make up that did nothing for her looks.
She had had plenty of lessons as a teenager, had been close to driving test standard but had stopped, due to a family problem and only recently taken driving up again. Despite that she was a good driver and very competent. She did not say much, and it was left to me to make conservation as we got to know each other better over the weeks.
Over the weeks I learned Jess was engaged, he had been her only boyfriend and was a technician in the RAF and currently away for a few months in the Falklands. I told her I was married for the second time and had three children. The house was her parents and her nan lived there too.
It was always a rush for her she confessed, literally she got off the bus from work and straight into the driving seat. Could she have a later lesson. Her last instructor would not change things for her. It would mean finishing later than I wanted but agreed to change her lesson to a later evening slot that suited her.
The following week, I pulled onto the drive. A few moments later Jess came out with the redhead I had seen before. The redhead eyed me as she passed and flirty smiles were exchanged as she walked out onto the road. I was surprised at Jess’s plainness. She was wearing a tatty pair of jeans and similar jacket over a plain dark t-shirt. Her long dark blonde hair was loose, and she was not wearing any make up. She looked completely different and plain and that for some reason excited me. She looked sexually appealing and turned me on rapidly.
Jess commented on my expression and strange looks I was giving her. I told her she looked good and had surprised me with her attractive looks. She said something about me just saying that, but I took a risk and without thinking told her she looked so good it had aroused me. She took the briefest of looks and checked out the bulge in my trousers then smiled with a little embarrassment.
I thought I had offended her as she was unusually quiet and said nothing as we went round on the first hour of our two-hour session. I found the courage to bring the subject up and apologised for being out of order.
Jess laughed saying she was not offended but flattered she had made me like that and confirmed she was no prude, then added my bulge looked rather impressive. She changed the subject and we continued going round the circuit. We headed back towards Dorking, but there was something I needed to her to catch up on and told her to come off the A24 by-pass and pull into the bikers’ café.
I took the opportunity to get her to do some reversing and bay parks then told her to park up. I told her to relax and remove her seat belt so that we could do some oral. It was the wrong way to put it. Jess looked at me a little shocked. I beg your pardon she said, that’s inappropriate, and told me she and I were spoken for and asked what I was playing at suggesting such things.
I must confess I laughed when I realised what I had said. She did not find it funny at all until I explained I meant we should do some Q & A for her up and coming test in a couple of weeks. She laughed at her own mistake. I then told her I would love to give her oral if she wanted. She looked at me and inquisitively asked did I say I would give her oral.
I told her yes and added I would treat her to my bare married cock and not pull out of her either. Her face was one of surprised shock. I was certain I caught a hint of aroused pussy as she playfully slapped me in the arm saying that was crude and naughty. The lesson recommenced with me asking the Questions and correcting her on some answers.
We got back to her house and Jess told me she was busy the following week and not sure about the week after as she thought she would be away on a work course. Her driving test was a few weeks or so after that. She would phone the office to book another lesson when she returned. I had obviously gone too far. She would make a complaint and probably get another school to take her for her test. Damn.
I waited to be called into the office about my conduct, a day passed, then a week, but nothing. It had been three weeks and I had forgotten about Jess. Then the office phoned telling me she had booked a two-hour lesson for the Sunday evening. I had mixed feelings as I pulled up her on her drive and waited. She came out looking rather stunning I must say, she had put her hair into plaits and wearing simple flowing lacy top and loose-fitting trousers.
My cock was solid as she slipped into the driver’s seat. I complimented her on her hair style. Her eyes scanned my bulge and she had a little grin as she checked out my bulge making it obvious, but I kept it professional and made a start on the lesson plans.
Her driving was not at her usual standard, she had something on her mind. As we drove, I asked if everything was okay. She told me she had not had sex for ages and wondered if I would give her oral, just oral in the car and she would jerk me off. I told her to drive somewhere quiet if she wanted to find out. Jess looked uncertain.
I was not certain either, it was just a hopeful comment with the expectation that it would go no further. We were close to Chessington theme park. She pulled in and parked up in a corner face in. She became extremely nervous. She was shaking slightly as she looked at me. She composed herself and then crudely asked if I was teasing her or going to eat her c**t out.
My car was a sort of smaller version of an MPV, Jess unzipped her trousers and sat on the middle rear seat with the seats set back slightly. She did not want any kissing and told me what I could and could not do to her. I sat next to her right side but to the side exploring her breasts through her top with my right hand. She was not wearing a bra. Her breasts were a fair size and I wanted to suck them but that was not allowed.
I slipped my left hand down and pushed my hand inside her knickers and felt her trimmed pussy hair. I spent a moment rubbing through her mound intently and teased over her lips. I pushed a finger in-between her damp lips and explored her wetting inners adding a second finger and found her clit and strummed on it with a thumb fingering her at the same time.
