Jack. A Journey of Discovery

Part 1 chapter 1. Jack gets educated.

Aged 21 Jack was finally released from Bedford prison, 6 years after he was originally sentenced to 3 years to Borstal in 1968. His sentence was extended several time's and eventually, at 18, he was sentenced to 3 years in prison for GBH.

3 other prisoners had thought it a good idea to attack Jack in the shower a few days before he was due for release. The court was not impressed with his claims of self-defence, as they were shown pictures of a broken chair used to beat the men, after Jack had knocked them down. One of the legs covered in blood, from being forced into the gang leader's arsehole, got Jack the maximum sentence of 3 years.

Jack was denied parole twice, so today he was a free man, as he had served his entire sentence. Walking through the large gate of the prison, Jack swore he would not be back. Walking into town with no real idea of what to do next, he considered heading to his hometown. As he had not had a single visit or letter from his step mum and dad, he thought there was little for him in Barnsley. Jack had not seen his real mum since he was 5 and could barely remember her but knew her name was Kirsty Jones and she was originally from Luton.

After wandering around for a while, Jack concluded that life was not much different in 1974 than it was in 1968. Seeing a sign for the rail station he made a snap decision to go to Luton as Bedford did not seem to have much of interest to him. As he walked, he admired a new shape Ford Cortina as it drove past. Idly wondering if they were as easy to steal as the old cars.

As he watched the driver of the Cortina parked in a long term car park and ran from the car, dragging a suitcase, towards the station. Walking into the car park he ripped out an old steel coat hanger that was being used as an aerial on an old mini.

Straightening the wire hanger out, he bent a hook into one end and casually walked up to the Cortina. Getting his fingers into the top corner of the door he pulled and fed the wire into the small gap. A quick glance around confirmed nobody was watching as he looped the hook around the button to unlock the door. Several kicks broke the plastic housing for the ignition, to his amazement the ignition wires were the same colours as they were on cars from years ago. Within a minute the engine was running and using all his strength and weight on the steering wheel, he had broken the steering lock.

Taking his time, Jack carefully looked around the car. It was brand new, with less than 500 miles on the clock and had a full tank of fuel. In the glove box he found a folder with the service book and handbook in it, and unbelievably the spare key was tucked into a plastic side pocket. Using the key to unlock the boot, he found a bag full of clothes a briefcase and a map book.

Putting the map book on the passenger seat, he pulled out of the car park, realising he had no idea where he was, he shrugged and turned left. Stopping at a car parts store he bought some insulation tape a set of plyers and a screwdriver. Asking for directions to Luton the guy in the shop drew him a little map. Getting out of town, he found a layby and repaired the ignition surround and wiring. Just in case he got stopped by the old bill or some curious onlooker noticed the smashed plastic.

About 40 minutes later, Jack drove into Luton and found a cheap B&B with off road parking. Remembering the guy pulling a suitcase, Jack reasoned that he had at least 3 or 4 days before the car was missed, maybe a week and decided to keep the existing number plates for the time being.

Paying the Landlady £5 for 2 nights in advance ate into his money. He had been given £13 discharge money, £4 travel and a fiver that he had when he was arrested, £22 was not going to last very long. That evening, he took the landlord up on a hot meal for 25p. She was a pleasant lady, in her early 40's he guessed. That evening there was just her and Jack at dinner. Her name was Gwen and Jack enjoyed her idle chatter over dinner, until she suddenly asked.

"How long you been out of prison lad, very nice car for such a young man," she giggled.

"Yeah, I have borrowed the car for a few days, what makes you think I been in prison," Jack asked.

Laughing softly, Gwen ruffled his hair, "Never try to con a con artist, borrowed the car" she said with a grin,

"Ok, i was released this morning and I had done 6 years, I didn't fancy the train." he admitted.

"6 year? Wow, but you're so young." She gasped.

"3 borstal, 3 in Bedford prison." Jack said.

After dinner, Jack had thought about having a walk around the area but agreed to help Gwen wash up. Jack washed as Gwen dried and put stuff away, there was a lot because she said she only washed up once a day.

Jack was sure that Gwen was deliberately squeezing past, her hand brushing his arse and her blouse button was undone, exposing her generous cleavage to his greedy eyes. Deciding to try his luck, he ran his wet hand down her back and patted her arse. Apart from complaining about his wet hand's, she did not seem to object, so he moved his hand and stroked her generous breasts.

"You ever been with a woman Jack," she asked.

"No, I was locked up before my 15th birthday, so never got a chance," he said as he tried to adjust his painfully hard cock.

Taking him by the hand she led Jack through to her private room, that was 2 rooms and a small bathroom. Pushing him back on the bed she undid his jeans, releasing his rock-hard cock. Jack had noticed that his cock seemed longer and thicker than the other boys and men in the showers and Gwen confirmed it.

"Fuck me I was going to give you a Bj, but fuck that," she said as she rucked her skirt up, pulled her panties to the side and started to feed 8" of solid cock into her soaking wet pussy. For Jack it felt tremendous as his bulbous bell end slipped inside her and he could not help but buck his hips, Gwen howled and moaned as his cock ripped her pussy open and after a 2nd thrust, he was deeper in her than any man had ever been. A third thrust and his pubes clattered into hers, igniting waves of pleasure deep inside her.

Holding her arse up, he hammered his cock as fast and as hard as he could as she yelped and shook above him. Feeling himself starting to come he doubled his efforts and poured a heavy load deep inside her, disappointed it was over, but relishing the feeling of her pussy clamping onto his cock as she squealed and her whole body shook.

He fucked her twice more before going back to his room and falling into bed at about 3am. He woke up about 10am as Gwen let herself into his room, and took his soft cock in her mouth and caressed his ball sac as she knelt on the bed. Sucking him hard, she said that his cock was giving her jaw ache as she moved to straddle his hips. Pulling her to the side, Jack forced her legs wide apart and lowered his head between her legs and studied her pussy.

Her scent was intoxicating and as he ran his tongue the length of her slot he decided he loved the taste and pushed his tongue deep into her hole, causing her to groan. Jack had heard all about a clit and how hard it was to find, so pulling back a little he asked her to show him her clit.

Reaching down she pulled her lips apart and up, and he saw it, his 1st clit a slightly different coloured nub in the deep pink folds of her cunt as it slid from its hood.

"Show me how you frig it, want to watch you come," his voice strengthening and tone demanding.

Hesitantly at first, feeling strangely exposed, Gwen did as she was told. As her excitement grew, so did her confidence as she plunged 3 fingers deep inside her, before resuming the rhythmic strumming of her clit. Jack was fascinated as he watched her orgasm, her pussy flared open and snapped shut as her slightly opaque juice pooled onto the bed sheet.

Quickly moving up her body, his cock bumped into the side of her sex before sliding balls deep into her still quivering hole. Grabbing her legs he pulled them up around his shoulders and ignoring her pleas and cries of pain he violently fucked her. Her orgasm as she came again was every bit as violent, her nails drawing blood on Jacks back, his cock bucking and jerking as he shot his load in her deepest places.

Collapsing into a sweaty heap, their breathing gradually returned to normal. Looking at his flaccid cock, covered in a mixture of girl cum and a smear of blood, he pushed her head down and told her to clean him up. Pulling her around, so she straddled his head, he studied her open pussy as she licked and sucked him clean.

Grinning to himself he roughly rubbed her clit in a sawing motion, it was as if she had been electrocuted as she shot forward, begging him to stop. Ignoring her pleas, he pulled her to a kneeling position and rammed his semi hard cock into her. After a few hard strokes, his stomach slapping against her arse he withdrew and shoved 3 fingers into her gaping hole. Scooping her juices up, he pushed a finger then 2 deep into her arse hole.

Her screams of pain only spurred him on as his cock probed the bud of her arse and he forced a few inches into her tight hole. After a few strokes he decided he preferred the silky softness of her pussy, withdrew and bottomed out in her soaking pussy. Banging her hard and fast as she yelped and shook, he dumped another load into her sodden cunt.

When they had recovered, she moved to lick his cock clean, pushing her away,

"I need breakfast and a cup of tea. I am going to take a shower, will be down shortly. Full English," he demanded as he walked towards her small bathroom.

As Jack ate his breakfast, Gwen sat opposite him on one of the old armchairs.

"Did you like watching me do myself?" Gwen asked

"Yes, very much," Jack grinned

Draping her legs over the arms of the chair and scooting her arse forward so her pussy was on the edge of the seat cushion, Gwen asked,

"Would you like to lick me, or watch me finger fuck myself? I don't know what you have done to me, but I need to cum again." She said with a wide grin as her finger ran the length of her pussy.

Grabbing the large vinegar bottle, Jack passed it to her. At first Gwen pushed the narrower end of the bottle inside her but soon turned it round and forced the bottle deep inside her. Moving her hands so Jack could see she had got most of the bottle inside her.

Dropping to his knees, he fucked her hard with the bottle, her long sex lips stretched around the glass as he forced it deeper with each thrust as she scrabbled at her clit. Eventually the bottle hit something solid at the very top of her pussy, causing her to scream in pain and ecstasy as her orgasm swamped her. Leaving the bottle inside her, he watched with fascination as she recovered and her pussy pushed the bottle out. Jack read the morning paper as Gwen went off to clean herself up and get dressed.

"Is that motor ok to use, could do with going shopping, can I drive." Gwen asked.

As Gwen drove Jack noticed her short skirt had ridden up, exposing her thighs. Reaching across his hand slid between her legs, his fingers finding her wet and freshly shaved pussy. Finding the hard nub of her clit, Gwen wailed as her orgasm crested as she waited for the lights to turn green.

Parking the car, she reached down and took her panties off, spreading her legs wide so Jack could see her smooth mons and swollen sex lips. Do you like me shaved? I love it smooth, feels so nice and clean she murmured. As they walked around the market Jack took every opportunity to grab a finger full of smooth pussy. Eventually pulling her behind a stall he banged her hard and fast, spaying a heavy load deep inside her. As he withdrew, he noticed a stall holder had seen them and was rubbing a large bulge in his jeans. Gesturing to him he took sloppy second's and fucked her hard and fast. Gwen seemed to cum again as the old guy's cock jerked and spasmed as he sprayed his load deep in her sodden cunt.

"Oh my god, that was fucking amazing, it's always been a fantasy of mine to let a stranger fuck me on the street while I was still full of spunk from my boyfriend" she laughed as she wiped a dribble of spunk off her inner thigh before straightening her skirt and heading back to the car. In the Car, Gwen reached across the car and kissed Jack deeply.

"Thanks Jack, that was amazing. I just want you to know that I will do whatever you want me to do," she said with a huge grin spreading across her face.

As Gwen drove out of the carpark Jack said that they should get some new number plates for the car soon as it was 3 days since he had boosted it, nodding, Gwen said they should go and see her brother as he might be able to help with the car. As they drove Jack told Gwen about Kirsty Jones, his mother, and how he had vague memories of a sister.

"Hmm I used to know a Kirsty, don't know what her last name was, unusual name though, think my brother knew her as well." Gwen said, as she accelerated onto a dual carriageway and then braked heavily to turn onto a small track.

The track led to a small farmhouse, where they were greeted by 2 barking and snarling Rottweilers who encircled the car.

"It's ok, Jake doesn't like visitors, he will be out in a minute." Gwen laughed at Jacks alarmed look as one of the dogs put its front paws on his side window.

Jake, Gwen's brother, was extremely interested in Jacks story about the car. After a quick look around and doing a double take at the mileage he offered £400, quickly increasing it to £475 after a glance from his sister. Eventually, Jack settled on £100 and an old Rover 2200, that Jake swore was 100% straight, had a strong engine, a long MOT 2 months tax. Jake added that he would get him a fake driving license. Gwen asked him about Kirsty Jones,

"Oh yeah, haven't seen her in a while though, think she still lives in Leagrave in a flat above the Sugar Loaf pub. Her daughter can be found most nights down near the station."

Chapter 2, Hard reality.

Taking a dodgy insurance certificate and money, Gwen pecked him on the cheek and promised to come and have lunch with him soon as she reached down and playfully grabbed a handful of cock.

The Rover was a great old car and as Jack drove along the dual carriageway, he was impressed with the armchair like seats the wooden dashboard and the old car had a turn of speed, as the speedo nudged 80. Gwen knew the Sugar Loaf, and they parked in the car park just as the landlord was locking up.

"Hi George, is Kirsty about," Gwen asked.

"Hi Gwen, yeah she is home. What you want with that old slapper?"

"Need to have a chat, nothing heavy.

" Well remind the bitch that her rent is due," George laughed."

Walking up the steel staircase, Jack was starting to wonder if trying to find his mother was such a good idea, Gwen banging on the battered door at the top of the stairs interrupted his thoughts. The woman who answered the door, was a tall blonde with piecing blue eyes who looked like she had just woken up. Wearing a nightdress that was almost sheer and only just reached her thighs, Jack could clearly see her large breasts and a dark triangle between her legs.

"Oh hello Gwen, why the fuck are you banging on my door." She slurred.

Gwen moved fast and pushed the woman back into the surprisingly tidy flat. Leaning in close she snarled,

"My friend has some questions for you, if I think your lying, well you know what I mean."

Surprised at Gwen's words, Jack sat next to the woman and just said.

"I think you are my mum,"

"Oh my god, is that you Jack, that scum bag that you call dad, just disappeared with you, left me at just 23 with a 6-month-old girl. There's hardly been a week gone by where your sister and I haven't wondered where you were and what you were like." Kirsty said as she dissolved into. tears.

"I have a sister?" Jack asked.

"Yes, she is asleep now as we have to go to work tonight, as the rent is due tomorrow."

Disappointed that his mother and sister were prostitutes, he almost walked away. Deciding that with his record he should not judge anyone, he continued and soon they were chatting freely. His mum had made no attempt to cover her nudity, and Jack was embarrassed to feel his cock growing painfully hard as the hem of her nightdress rode up

Gwen interrupted, "look what you, done to your son, pointing to his swollen crotch. Best we turn the clock back a few years and give the lad a good show," she giggled

The 2 women had been lovers for years, and after some initial kissing and petting they moved into 69. Gwen skilfully arranged it so that Jack could see everything and pulled Kirsty's hairy pussy apart, his eyes feasting on the spectacle before him. Gwen moved between Kirsty's thighs, her face mashed into Kirsty's cunt as she waggled her arse invitingly at Jack. Moving across the room he dropped his trouser and rammed his cock balls deep in her sopping wet and open pussy. As he thrust into Gwen, he watched as she feasted on Kirsty. Very quickly his mum started to cum and cried out as her orgasm crested. It was all too much for Jack and he blasted a heavy load deep inside Gwen.

"What the fuck is all the noise," a female voice yelled as the lounge door burst open and a young woman came into the lounge. She was nude, her brown hair dishevelled her sleepy eyes opening wide as the scene unfolded before her.

Oh, hi Gwen looks like I missed the party," she giggled

"That's ok Ruth, meet your brother Jack." Gwen said as she leaned over to suck and lick Jacks cock clean. To Jacks amazement he felt his cock start to swell as he drank in his sister's body. She was very pretty, like her mum she was blonde with piercing blue eyes, pert tits rode high on her chest and were topped with large pink nipples her flat stomach led to the swelling of her shaven Mons and clearly visible long sex lips.

"Oh, dam girl seems he likes your looks, his cock gives me jaw ache when he gets hard, think you better come squeeze another load out of him!"

Without hesitation Ruth frigged herself as she walked across the lounge then turned around and sat on Jacks cock. Spreading her long lips with her fingers she gradually took his length as she rode him, reverse cowgirl, leaning forward so he could see her pussy stretched tight around his cock. Gwen motioned Kirsty and she straddled his head and frigged herself as Gwen fondled his balls. As Jack started to come, Kirsty's orgasm was sweeping over her, lowering herself onto Jacks willing mouth as her pussy overflowed with girl cum. It felt strange, knowing that he was fucking his sister and feasting on his mother's cum laden pussy, but as his cock erupted inside Ruth, he knew he wanted more.

As they all laid in a sweaty heap, Gwen explained that the guest house used to be a knocking shop, that her mum had started in the late 50's. Jacks Mum and sister had worked there for years before the old bill just got too interested in the place. Apparently, Gwen was the madam and was very good at organising sex parties for influential people. Getting up Gwen said that we had to go as some of her guest's had requested dinner and Thursday night extra's. Asking Kirsty how much her rent was she gave her £45, added a tenner for grocery's and said she expected them at the house tomorrow morning at 9am.

As Gwen drove home, she explained that Thursday nights got a bit busy in the house as it was payday at a local factory, so there would be plenty of willing customers for her and a couple of other women. Going onto explain that she owned the house next door and organised a card school and a full-service massage service a few times a month. All the rooms have strategically placed peep holes if you would like to watch, she grinned.

After an early dinner, Gwen introduced Jack to a few people as she showed him around. One of the girls, Suzy was a stunning looking black woman, the other an older woman called Jane. Taking Jack up into the Attic, Gwen explained that it cost £5 to get in and a massage was £15, £2.50 of that was kept by the house. The attic ran the entire length of both houses, and every bedroom had a tube installed for a peep hole. Taking the cover off one of them, Jack saw a bathroom and watched Suzy taking a piss and then shaving her legs and trimming the tight curls covering her pussy with a small pair of scissors.

By 7 pm, the house was full of people and the card school got underway. At around 9pm they stopped for a break and Gwen served sandwiches and beer. Suzy and Jane had been joined by a third woman who was called Grace. Noticing me watching, Gwen said she thought that Grace was his mum's sister and suggested he should go to the attic as the girls would be getting busy soon. The party lasted most of the night, as people left and others arrived.

Jack was amazed by the amounts of money on the poker table and the girl's stamina as he tried to keep score on each woman. By 4.30am the party was breaking up and Jack reckoned that each woman had serviced about 12 men each, although he thought that Grace had done 15. It seemed that £15 got around 15 minutes with the girl and consisted of a quick massage, and then oral or full sex according to the customers preference. Sometimes the girls only had about 15 minutes or less between customers.

As he was about to go downstairs, he heard voices in the room below him, opening the peephole he saw all 4 girls and a middle-aged man. His session lasted a lot longer than 15 minutes and jack thought that he had sex with all of them before finally finishing inside Jane as Grace sat on his face and Gwen and Suzy stroked and caressed him. He also noticed that the guy wasn't wearing a condom, and the women seemed a lot more attentive and interested in his every need. Falling into one of the beds in the loft, Jack was asleep in moments.

He was woken at 8.00 by Gwen, holding a cup of coffee and a plate full of sandwiches.

"Morning, did you enjoy the show? Next time I will include you on the guest list if you want."

As he ate, they chatted about the evening, and Jack asked about the guy he had seen all 4 of them service.

"Oh, he's our eyes and ears in the old bill, he looks out for Jakes business as well."

Anyway, an evening of pretending to enjoy sex always make me proper horny Gwen grinned, as she stroked Jack through his Jeans. As his cock burst inside Gwen's grasping cunt as she came for the 2nd or 3rd time, he really couldn't believe his luck as he fell back to sleep.

Hope you enjoyed my story, comments and suggestions welcome as always. Part 2 to follow.