This story has been adapted from entries from diaries entrusted to me after my mother’s death. I have ‘changed names’ to protect the innocent or guilty depending on your point of view and I have added a little bit of poetic licence to add substance. This is by no means meant to denigrate her memory but to share a little of the real sensuous, broad-minded woman I discovered her to be.
My mother suddenly died ten years ago shortly after her sixty-sixth birthday; years before she had promised to leave me some mementos of her life. Over the years Mum had collected items for each of her children in boxes with our names on them but when my sisters had been through her things they had not found anything specifically left for me although they had each had a box addressed to them. Then a few weeks ago my youngest sister rang saying she had found a locked box in the loft with my name on it and a note with a key in an envelope. The note said the box was for me and it should be given to me only after my Mum’s death.
The boxes my other siblings had received contained pictures, school reports, birthday cards nothing controversial just silly mementos collect by a doting mother over the years. So although curious my sister did not open the box or tell my other two sisters who would have looked inside just to spoil any surprise. I thought I knew what was inside and I knew I could never share it with anyone else as they would never understand.
My mother and father were almost worshipped by my brothers and sisters and they spoke about them as though they were a conventional and very much in love couple with no dark secrets. I knew a different story; admittedly they were very much in love but they had a secret unconventional sex life.
I had become part of their sex life when my dad had been ill and unable to satisfy my mother’s needs. It was during that period of time I had become my mother’s lover and she took me from an inexperienced boy to a sexually confident young man. My experiences with my mother became my benchmark for exceptional sex.
She had confided in me that she kept a diary of all her experiences from her very first sexual contact. She had only ever shown the diary to my Dad but she described some of her more notable encounters to me as a prelude to us making love; a little like verbal foreplay. Mum refused to tell me how she lost her virginity or to who but did say it wasn’t my dad she also promised that one day she would give me her diary to read when she felt the time was right.
As I drove over to my sister’s house to collect the box I thought about that time as my Mum’s lover and my cock responded as it always did becoming stiff and remaining that way until I pulled up outside. I had to pretend to be on the phone as I waited for my ‘bone’ to subside enough to be able to greet my sister.
I hadn’t told my wife that ‘my box’ had been found as I needed to sanitise the contents before she saw it. Luckily I had work commitments which meant I had to be in Nottingham for the rest of the week and had time to view the contents in private.
Five hours later I was in my hotel room with the box in front of me on the bed reading a letter from my mother. In the letter she confirmed that her promise to me would be kept as the box contained her memoirs and mementos she had kept from her life with my father. The box contained the same bits and pieces my siblings had been given but also a number of diaries and dozens of packets of photographs. Each packet of photos had a reference number on it which I later found corresponded to a section of her diaries. The letter contained a final passage which was a last instruction which read ‘this box contains my most cherished memories including my first time and I wanted to share these with you and no one else. We had a special love only a mother and son could have and only you rivalled your father in my heart. I loved your brothers and sisters but you have always been my special baby boy and the intimate times we had were among the most special of my life. The memories are for you to read and enjoy but then they must be destroyed.’
The diaries dated from 1954 just after her eighteenth birthday and contained entries listing dates with boys her own age and details of early fumbling and heavy petting sessions. My Mum and her best friend Alice appeared to have a great time most Friday and Saturday evenings teasing different boys. One entry described how she and Alice had met with three boys one Saturday afternoon in the summer and went swimming in a local river near Reading. Later the boys had plied them with cider and taken them to a barn and persuaded them both to strip naked. One thing led to another and while Mum had been petting and rubbing the cock of one of the boys Alice had actually sucked the other two boys. The early writing seemed quite naive and the language used fairly innocent but as the entry dates headed past Mum’s nineteenth birthday more explicit language appeared and the descriptions more graphic. She had noted down that on Alice’s nineteenth birthday a couple of weeks after her own that they had spent the night in a hotel room with two boys where Alice lost her cherry to Harry.
Mum described how she and the other boy Fred had got into bed together naked and she had sucked her first cock but she didn’t let him spurt in her mouth. She didn’t go all the way with him although she had let him finger her but was disappointed that she hadn’t come. She had also made the first note about the size of the cock she had handled saying it was no more than a hand-width long.
Mum was a quite petite woman 5′ 1″ tall at best, but she was nicely proportioned with slim legs and a 34C bra size. I tried to remember how big Mum’s hands had been and I was sure they were quite small. There was a grainy photo of Mum and Alice on a beach dressed in swimsuits posing like girls in the old beauty contests. Alice was taller and looked to have a similar bust size but fuller hips.
The next few entries suggested that Alice and Harry seemed to have become a permanent couple and Mum had often found herself alone when they had disappeared off to copulate somewhere. It hadn’t stopped her finding someone to walk her home and enjoy and little petting.
Just before her twentieth birthday she wrote about an encounter in quite graphic detail. Mum worked in a factory alongside my grandmother and her sister; my Aunt Joan. Mum worked on the shop floor normally, my grandmother worked in the canteen and my aunt worked in the finance office. Her friend Alice also worked in the office and had persuaded her to help with a stock-take and file audit one weekend just before the factory closed for their summer break. The office manager Eric Dromby had a reputation as a bit of a groper and Alice wanted to have someone with her if he decided to take advantage. Mum agreed as she thought it might lead to a cushy office job even if she would have to work with her goody-two shoes sister; she also quite liked to find out if Mr Dromby’s reputation was true.
Nothing had happened on the Saturday apart from Mum and Alice noticing that Dromby was watching them both whenever they were bending over or stretching to reach boxes. Before they left Dromby asked Mum if she was going to church on Sunday and before she thought why he asked she had found herself saying no and agreeing to come in to finish of the last few boxes as Dromby had mentioned that there may soon be a vacancy in the office. Unknown to Mum Alice had already refused using the excuse of going to church (although she actually had a date with Harry). Dromby offered them a lift home in his car as he lived in a small village close to the two girls. Alice leapt out of the car by her front door leaving Mum alone with Dromby he insisted on taking her to her house. Mum lived in a small cottage down a short narrow lane so Dromby had to pull up a little way from her door. They were out of sight of the house and Dromby reached across Mums lap to open the door for her and she felt his elbow brush against her breasts. Dromby placed a hand on her knee before she got out of the car.
“I’ll pick you up tomorrow from the bottom of the lane at nine o’clock, Miss Brimley,” he said.
“Wear a nice dress and I will buy you lunch in town as a thank you for helping out,” he added as she twisted her legs to get out.
“Thank you, Mr Dromby, I will see you in the morning,” replied Mum waving as he closed the door.
She noted in her diary that her nipples had stiffened when he brushed against her and later that night she rubbed her button and fingered herself to an orgasm imagining what Dromby might try to do to her the next day.
She rose early washed and put on her best silky camisole slip and French knickers under her prettiest dress; wearing the slip meant she didn’t need a bra underneath as it held her tits in place and the dress was also tight across her bust. Mum put on stockings and her only pair of heeled sandals; she felt excited as she waited for Dromby to arrive in his car. Although she knew Dromby’s reputation she felt safe he wouldn’t try to go to far as the other women (including her own Mum) gossiped about him being unable to do anything else since he was blown up in the war when the factory was bombed. Rumour was that his wife had run off with a soldier after she found out he couldn’t have sex; some of the women even suggested his cock had been cut off in the blast.
Dromby had limped since the bombing and sometimes used a walking cane when his leg played up; he had the cane with him in the car when he pulled up.
“Good morning Miss Brimley, you look very nice this morning,” he said through the open car window.
He reached across to open her door. Mum had to manoeuvre into the seat as he kept his hand on the door making her have to brush against his outstretched arm. Her nipples tingled as they hardened she was sure Dromby noticed them beginning to show through the fabric of her slip and dress.
“Thank you Mr Dromby, you did say to wear a nice dress,” she replied trying to sound shy.
They made idle chit chat during the drive to the office and apart from leaning across to open the door when they arrived Dromby did not try to touch her. Mum began taking the last of the boxes from the storage shelves as Dromby checked their contents. She could feel his gaze on her every time she bent to take a box of files from the lower shelves. There were three boxes on the topmost shelf well out of my Mum’s reach. She found a step ladder and placed it next to the rack of shelves. Dromby limped over to hold the ladder steady while Mum climbed up (his gammy leg prevented him climbing). She still could not reach without stretching and she felt Dromby place a hand on the back of her thigh to prevent her falling back. He still had his cane in the hand he held against her and she felt the top press against her buttock.
Mum took the first box and took a step back down and felt Dromby’s hand slid up her leg and the top of his cane catch her dress and lift it giving him a good view of her stocking tops.
“Sorry Miss Brimley I should have moved my hand,” he muttered.
He let go as she took another step down then placed a steadying hand on her waist as she stepped to the floor. Mum smiled without saying anything and took the box over to the desk; his touches and the cane pressing into the flesh of her buttock had sent a tingle through her and her nipples stiffened. Mum went back and retrieved the next box but Dromby only held the step-ladder this time. When Mum climbed up to get the last box she wobbled the ladder a little.
She gasped, “Oh Mr Dromby can you hold on to me I nearly fell off?”
She felt Dromby’s hand touch her thigh a little higher than before his cane pressing harder on her buttock. Mum stepped down allowing Dromby to repeat his earlier trick and she lingered allowing him a longer view of her stockings and a glimpse of her bum covered in the silky fabric of her French knickers. She felt the tingle again and a slightly damp sensation between her legs; so after putting the box down she excused herself and hurried off to the ladies toilet. She sat in the cubicle and dabbed the juices from her swollen pussy lips resisting the urge to touch her button.
When she returned to the office Dromby had made a pot of tea and suggested they take a quick tea break before cataloguing the boxes. As they sat sipping their tea Dromby struck up conversation by asking if Mum was ‘seeing a young man yet’.
“No one steady,” Mum replied trying to sound as shy as possible.
“I’m surprised you don’t have a young man as you are a very pretty girl and I noticed you have nicely toned legs; do you cycle a lot?” he asked.
“I cycle to work every day when I work on the factory floor as I have to wear overalls all day, but if I dress up I get the bus into town,” she replied innocently.
“Well if you come to work in the office I would expect you to dress correctly so you will need to take the bus. Of course we would need to make sure your pay rise takes into account the extra fares.” He said.
“Do you have lots of nice dresses suitable for the office?” Dromby asked.
“I would need to buy some more nice clothes and shoes too,” replied Mum.
“Indeed, we can’t have you wearing overalls so I think we could let you have a small loan to buy proper office clothes and stop it from your future wages,” Dromby remarked.
“Do you wear stockings with your overalls?” Dromby asked.
Mum smiled, “No silly they would ladder on the rough material!”
“Quite, so you will need to get yourself a few nice pairs of stockings too. I hear they are still quite an expensive item?” he said.
He was not looking directly at her but down towards her lap where the hem of her dress was above her knee.
“Yes they are expensive but not as dear as nice silk underwear. I prefer to wear nice underwear in the summer as it keeps you cool. But it gets ruined under the overalls so it would be nice if I got the job in the office to be able to wear nice underwear and stockings every day,” Mum replied.
She stood up and carefully smoothed her dress over her body and legs.
“Should we start on these boxes now?” she asked.
“Yes, you are right. Interesting as it is; we can’t spend all day chatting about ladies underwear,” Dromby joked.
“I’ll show how to categorise the files and then we should get through them in half the time,” he said.
He patted the chair next to him indicating Mum needed to sit close. Dromby laid a file on the desk in front of them and showed her how to follow the cross reference by taking her hand and tracing the grid inside the front cover. Mum had to lean closer to reach so Dromby put his arm around her waist and rested his hand on her hip. Mum didn’t push it away so he gripped her a bit firmer.
“I hope no one comes in, they will wonder what we’re up to,” smiled Mum.
“You don’t mind do you; only it’s easier to show you this way,” said Dromby.
“I won’t tell if you don’t,” she replied.
“The women on the shop floor are terrible gossips and I would hate to get a reputation as a tart,” Mum said.
“I know they are and I know what they say about me; so this will be our little secret,” agreed Dromby.
Mum felt his hand move to her thigh and give it a squeeze.
He deliberately showed her a number of times how to get the files ordered each time grabbing a little bit more flesh. Eventually he let her sort through the boxes on her own and they soon had them all categorised and Mum began labelling the ones for archive and placing them to one side before re-stacking the others on the shelves. The boxes went on the shelves in order of age oldest on the top. So when the final boxes were left there were four that needed to go on the top shelf. Mum asked Dromby to hold the step-ladder like before and to steady her legs as she reached up.
Dromby seemed less reserved now he thought Mum was more compliant and she felt a firm hand squeeze her thigh just below her buttock. Mum deliberately stretched up to let his hand rub her thigh as she eased down Dromby’s hand rose up and grazed her buttock which he cupped and squeezed. Mum gave a little gasp but immediately stepped down forcing his hand higher; this lifted the hem of her dress exposing her stocking clad legs for a second time. Dromby’s hand held the fabric as she took another step down raising her dress higher over her bum exposing her French knickers.
As she reached down for the next box Dromby let her dress fall then touched her arm.
“The next boxes are awfully grimy; you don’t want to get that nice dress dirty, why don’t you slip it off?” he suggested.
“I don’t know if I should, what will the women say about me if they found out I had stood in your office just in my underwear?” Mum said trying to appear as timid as possible.
“As much as I would like to see you in your underwear, Miss Brimley, I meant you could change into an overall,” Dromby said.
“My overalls are at home, I don’t have one here,” said Mum.
“If I did take my dress off, you promise not to tell anyone?” asked Mum.
“As I said before, it will be our little secret and I will wait outside if you are shy?” replied Dromby.
“But you need to hold the ladder steady in case it wobbles. You promise not to tell anyone?” asked Mum again.
“A gentleman never tells tales on a lady,” Dromby said with a smile, “and it’s not as if I haven’t seen a girl in her scanties before!”
“Okay I don’t want to get my nice dress messy,” declared Mum.
She unbuttoned the top and wriggled the dress off her shoulders. She heard Dromby take a breath as she pushed the dress to the floor and stepped out of it. She folded it neatly and placed it on a chair before stooping to pick up the next box. She knew Dromby was getting agitated and so she bent forward to give him a good view of her silk clad bum. The thrill of making Dromby excited had a similar effect on her and she felt her pussy lips moistening again.
As she stepped on the ladder Dromby’s hand was immediately touching her waist and the familiar tingle spread through her body. She suddenly started wishing he would hurry up and grope her properly as all this play acting was just delaying the inevitable. But they went through the same routine of her stretching and him touching as before only each touch was a little firmer. When the last box was on the top shelf Dromby had both hands on her waist as she stepped down and he pulled her back into his body and she felt him slip his hand under her camisole and touch her bare flesh making her flinch.
“Don’t be frightened Miss Brimley I won’t hurt you,” Dromby whispered.
“I’m not frightened Mr Dromby, but haven’t done this sort of thing before,” lied Mum, “I don’t want to be spoiled before I get married.”
Laughing Dromby said, “I won’t do anything you don’t want me to, but a man likes his wife to have some experience on her wedding night. I think you quite enjoyed being touched earlier; did it feel nice?”
“Yes, it makes me tingle,” she replied.
“But isn’t it wrong to go too far before you get engaged?” she asked.
“As long as we keep it to ourselves no one will get hurt,” said Dromby.
He slipped his hand further up under her camisole a cupped her breast. Mum gasped then moaned softly and allowed him to pull her closer. He kissed her neck and she sighed but didn’t stop him, then he guided her to the desk, sat down and pulled her onto his lap.
“You have lovely titties Miss Brimley. Take off your camisole so I can see them better,” ordered Dromby.
Mum lifted the camisole over her head and exposed her breasts; Dromby pinched her nipple and she groaned with pleasure and felt juice leak from her pussy.
“There you are; I told you that you will enjoy it,” he whispered.
Still playing with her nipple with one hand the other slid along her thigh easing them apart until he touched the damp gusset of her knickers. Mum couldn’t stifle her moans as he touched her so intimately.
She breathed in this ear, “Oh that is nice. Should I take off my knickers for you?”
“That would be perfect Miss Brimley, slip them off but leave your stockings on and kneel down in front of me!” he replied.
As she took off her knickers Dromby marvelled at her thick curly pubic hair which glistened with moisture. Mum knelt down as he unbuttoned the fly of his trousers and pulled out a tiny cock.
“Now put this in your mouth!” he said slightly raising his voice.
He pulled her head forward as Mum opened her mouth and tried to hold his cock steady but it was so small she had to push her face into his groin and trap his cock against the roof of her mouth with her tongue.
Dromby held her head and rocked it back and forth he began moaning, “Good Miss Brimley, suck it like an ice lolly!”
After about a minute of sucking a groan came from Dromby and he held her head down as he spurted in her mouth.
“Suck it in Miss Brimley and swallow it is good for your complexion,” he ordered.
He finally released her head and she let his cock slip out of her mouth and looked up into his eyes.
She asked, “Was that alright Mr Dromby? I’ll do it again if it wasn’t!”
Dromby couldn’t believe how compliant this shy girl had become; none of the other girls had let him progress past feeling their titties.
“I need to recover young lady but sit up on my desk so I can see your opening. I will return the favour and make you feel nice. Have you ever touched yourself there?” Dromby asked.
“Sometimes before I go to sleep when I am feeling naughty I rub and put the tip of my finger inside,” said Mum.
“Have you ever had an orgasm?” he asked in a slightly out of breath manner.
“I don’t know,” Mum lied again.
He laughed, “Well let’s see if I can show you. I think from the way you liked having your titties touched I shouldn’t have too much trouble,” he bragged.
Mum thought he was going to put a finger inside her but he stood up, pushed her legs apart and moved between her thighs. Mum put her hand between her legs.
“You said you wouldn’t try to put your thing in me!” she said loudly.
As horny as she felt she wasn’t going to let him enter her.
“I was just making sure your legs were wide apart,” he said in a calm voice.
He took his cane and ran the rounded shaped ivory handle down her stomach. The head was smooth and bulbous tapering into the shaft. He eased her hand from her opening and rubbed the head over her pubic mound and pressed it against her sensitive clitoris.
A jolt of pleasure ran through her body and she groaned, “Ooh yes!”
Encouraged he increased the pressure and rubbed it up and down a few more times until she began actively trying to grind on to the tip. He slid the head lower and eased it into her opening and pushed easily breaching her pussy lips. Another gasp came from her mouth and she pushed her hips forward taking the head inside as her pussy lips moulded around the shaft. He smiled as her head fell back and she groaned deeply and panted.
“Yes push it in, it feels nice,” Mum moaned.
She pushed forward again then she felt the pain as her hymen tore but by now his thumb was rubbing her clitoris and she was close to an orgasm. The pain was masked as she came very hard and gripped Dromby’s hand holding the cane inside her. The pleasurable waves of ecstasy emanated from her vagina through her body making her breasts tingle and her nipples harden and tears leaked from her eyes.
She had never felt an orgasm as hard as this one and it seemed to last for several minutes. Dromby stared in amazement at the transformed girl in front of him as he struggled to withdraw his cane as her pussy gripped the shaft. The end was streaked with her juices and blood where he had taken her virginity; he panicked and began to apologise.
“I’m sorry Miss Brimley I didn’t mean it to go so far in. Are you okay?” he asked.
“Yes sir, I best go and clean up,” she replied.
Grabbing her underwear and dress trying to avoid eye contact Mum ran to the toilet and wiped her pussy. She was surprised how damp she was; it took a while before the slime from her pussy wasn’t streaked with blood. She felt sore but her pussy was still throbbing sending tingles up to her nipples. She dressed in the cubicle and washed up quickly running her hand through her hair. Her make-up was still in her handbag so she dabbed her eyes carefully not to smudge her mascara too much.
When she got back to the office Dromby had tidied his desk and adjusted his trousers.
“I think we are finished for the day Miss Brimley we can go for lunch and I will give you a lift home,” Dromby said.
“Yes I would like that or we could pick up a sandwich and drive to the picnic area in the woods as it is a nice afternoon,” she suggested.
Half an hour later they were parked in a secluded spot looking out over some park land just having eaten their sandwiches in silence.
Dromby eventually turned to Mum.
“I am sorry I might have taken it a little too far earlier Miss Brimley; are you feeling okay?” he said.
“I’m not really spoilt, am I Mr Dromby because it wasn’t you inside me just your cane?” said Mum coyly, “And I won’t get pregnant by swallowing your seed?”
“No you are still a virgin until a man puts his member inside you and you can’t get pregnant by swallowing a man’s seed,” he answered her.
Trying to make it sound an innocent question she looked Dromby in the eyes.
“Mr Dromby, when I get a job in the office will do you want me to do that every day?” asked Mum.
Dromby looked at her closely.
“It may not be every day that I ask you to look after me but I think you will perform your duties very well,” he answered.
“I liked the taste of your seed so I don’t mind if you want me to suck you every day!” declared Mum.
“I will arrange for you to transfer to the office after the summer break, two days a week at first then full time after two months so we can replace you on the shop-floor,” said Dromby.
Dromby reached in his jacket and took out his wallet. He took twenty pounds out and handed it to Mum.
“This is for your new underwear and office clothes,” he said.
“Oh and Elizabeth, this is our secret!” he added.
Mums diaries did not mention any further adventures with Eric Dromby and as far as I recalled Mum never mentioned working in the office. So I don’t know if Dromby kept his word and any further episodes were not worthy of mention. My aunt is still alive but I am not sure if it would be a good idea to ask about the factory and Mr Dromby. The next entry in Mum’s diary describes the ‘true taking of her cherry’ as she put it which warrants another extract to be written.