My First Cock - Cover

My First Cock

by Chris Crescent

Copyright© 2020 by Chris Crescent

Fiction Sex Story: The seeds of my future sexual preferences were sown by something I witnessed when I was twelve and just becoming sexually aware.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/mt   Blackmail   Reluctant   Anal Sex   .

The seeds of my future sexual preferences were sown by something I witnessed when I was fourteen and just becoming sexually aware.

My sixteen year old sister, Maggie, apparently thought she was home alone. Intrigued by some worrisome noises, I went to investigate. I found my sister in her bedroom with the door ajar. She was lying on her bed, her skirt bunched up around her hips and her discarded panties lying on the carpet. She was rhythmically pistoning a cylindrical household object in and out of her vagina. I have never forgotten the image, the sight of Maggie’s eyes shut and her face screwed up with ecstasy as the glistening object slid to and fro accompanied by her moans of pleasure. I felt guilty at watching the most private moments of Maggie pleasuring herself, yet I was utterly helpless to drag myself away. The rate of Maggie’s pistoning accelerated and her moans got louder until, thrusting the object in as far as it would go, she went completely rigid, apart from rippling stomach muscles, as she wailed out her orgasm.

As my panting sister’s face returned to normal, I made a discreet exit to the safety of my own bedroom to relieve my achingly-hard cock. Fortunately she hadn’t seen me, but I never again got to witness her masturbate like that.

Since then, I have always been jealous of girls having vaginas and being able to pleasure themselves that way. But although I didn’t have a vagina, I did have another hole to experiment with and that got me started with anal play. I even used the same type of household object that my sister had used, although not the exact same one. And I painfully learned the necessity of lubrication.

I discovered there was something uniquely satisfying about the sensation of being full inside, of something sliding in and out of my anus and rubbing against my prostate. I must have spilled gallons of cum during my school years. And yet in a way I found it not entirely satisfying, as though something were missing.

I was pretty sure I wasn’t gay. Like the other boys I chased after girls and, despite a lower than average success rate, I bedded a couple. It was fun, I lost my v-plates and I learned how to do a decent job of satisfying girls, but it wasn’t the mind-blowing experience some made it out to be. I could take it or leave it.

Throughout my three year stay at college, I had to share a room and didn’t have the privacy to continue indulge my anal fixation. However willing girls were there for the asking. I chased them half-heartedly, not too bothered whether I caught them or not. And when I did, I performed my manly duties for the sake of appearances. I learned to keep my anal preferences a secret after grossing out one conquest who hadn’t expected me to ask for a prostate massage when she asked what she could do to please me.

After graduation I landed a white-collar job with a large company whose headquarters were in a city not too far from my home town. I rejected the idea of moving back in with my parents because the rush-hour commuting would have been intolerable. instead, for an extortionate sum, I rented a one-bedroom city-centre flat that was within easy walking distance of work.

Initially money was tight so I couldn’t go out much and I certainly couldn’t afford working girls like some of my more senior colleagues. Instead I built up my collection of anal pleasure devices, using the internet to research and resource new experiences. I also learnt not to do too much too often, having to take a few days off work to recover from a ‘tummy upset’. Thereafter I instituted an exercise regime to keep my abdominal and sphincter muscles in tip-top condition.

After I’d been at the company a couple of years and my career was progressing nicely, I received the awful news that my aunt, who lived in the suburbs of the same city, had been found dead in bed after a fatal stroke. She was single when she died, having divorced a husband after a brief marriage, so my parents had to arrange my aunt’s funeral. I’d heard family rumours about my aunt’s sexual orientation but figured it was none of my business. She’d made me feel welcome the few times I’d ventured into the suburbs to visit her.

After the funeral, Maggie and I went back to our parents’ house for a conference. My aunt hadn’t left a will so her estate was inherited by her sister, my mother. My parents had to decide whether to rent out my aunt’s house or sell it. Both options had their pros and cons, but my parents were veering towards selling the place because they didn’t want the hassles of maintaining it and collecting the rent. Then, in a lightbulb moment, Maggie asked whether it would be practical for me to rent the house. My parents wholeheartedly endorsed the idea, and came up with a nominal figure for the rent provided I met all the bills and maintained the place.

Although it would mean a commute to and from work each day, my aunt’s house was well-serviced by public transport routes that would leave me only a short walk to and from the office. Having my net housing costs cut by more than half would leave me with enough money to buy a modest car and other luxuries. I readily agreed, and that’s how I came to be living in my aunt’s house.

The property was situated in a 1950s estate. Houses had been built either side of two roughly parallel roads that followed the contours of the hillside. At the last moment, the developers decided to insert a short perpendicular connecting road about halfway along, and my aunt’s house was first on the connecting road. As a result, the gable end of my aunt’s house faced the rear of a house on the main road, and both properties had much smaller gardens than normal, having a weird triangular sort of shape. Being uphill, my aunt’s house looked down on the house on the main road. Privacy considerations meant that my aunt’s property had no large windows facing the house on the main road. However it had a separate bathroom and toilet and the toilet had a small frosted window with an opener at the top, and that looked straight into a bedroom of the other property.

When I moved in to my aunt’s house, the house on the main road was occupied by an elderly couple. I’d been introduced to them when I’d visited my aunt, and they seemed nice enough. They were quite proud of their little garden whereas my aunt had laid hers entirely to grass for ease of maintenance.

As I settled in to my aunt’s house, it quickly became clear the elderly couple were not coping too well on their own. They were too proud to ask for assistance, but they did accept my help with a few minor things like picking up prescriptions and emergency shopping. It was no great surprise when the elderly couple conceded defeat and put their house up for sale and I was sad to see them go.

The house on the main road sold quite quickly despite the small garden. I didn’t even realise anyone had moved in until I saw them in their garden; a couple of woman perhaps a decade younger than my parents and a kid of indeterminate age and gender. The kid was dressed in boy’s clothing but had an androgynous appearance; hair longer than a typical boy but shorter than a typical girl, a pretty face and a slim figure. When the kid started kicking a ball around in the garden, decimating what was left of the elderly couple’s planting, I decided definitely a girl: no boy would kick a ball that ineptly!

With the kid’s lack of natural ability and the relatively long boundary fence between our gardens, it was inevitable that the ball would end up in my garden sooner or later. I assumed the kid would just hop over the fence to retrieve it so I was surprised when my front doorbell rang. When I answered the door, the kid was standing there.

“Please Sir, may I get my ball back?”

Dirty blonde hair, dark blue eyes and a smattering of freckles across the face. The kid was really pretty. But the voice was a dead giveaway, the sound of a boy in puberty.

“Hi,” I said. “You must be my new neighbour. My name’s Chris Crescent. I’m pleased to meet you.” I held out my hand.

“Um, hi,” said the boy, offering his own rather feminine hand, soft with no calluses. “My name’s Luke Jarvis.”

I took Luke’s hand and shook it. “A pleasure. As you’ve probably noticed, my garden’s low maintenance. If your ball comes over in future, just hop over the fence. No need to ask.”

“I’m sorry, Sir. I don’t think my mums would like that. They would consider it disrespectful.”

“Mums? Is it just the three of you or is your father moving in too? And please don’t call me sir, it makes me feel old.”

“Sorry Sir. My father was a sperm donor and I’ve never met him, though I’ll have the right to know his identity when I reach twenty one. I call my mums B and A - B for biological and A for abiological.”

“That’s very clever. How old are you, Luke?”

“Fourteen. I’m due to start at the Hollis Winfield Academy next Monday.”

“It’s got a good reputation; I hope you like it there.”

“That’s one of the reasons my mums moved here. Our new house is only in the second tier of its catchment area but my mums checked there were vacancies beforehand.”

Suddenly our conversation was interrupted by a woman’s voice calling out, “Luke, where are you?”

“That’s B,” said Luke. “Here Mum,” he called back. “I’m just getting my ball back.”

“Luke, I don’t want you being a nuisance,” the voice called.

“I think we’d better go and put her mind at rest,” I said to Luke. I led the way through the side gate into my garden and found one of the women anxiously standing close to the fence.

“Go get your ball,” I said to Luke. He scampered off towards his errant football.

“Hi,” I said to the woman. “Luke and I have just been introducing ourselves. You must be Mum B.” The resemblance to Luke was clear. She was a very attractive woman and, despite her being some fifteen years older than me, I certainly wouldn’t have kicked her out of my bed.

The woman laughed. “No, it’s just B. My name’s Laura Jarvis. As you’ve probably noticed, I’ve just moved in with Luke and my partner Becky.”

“I’m Chris Crescent. This used to be my aunt’s house. After she died from a stroke, my mum inherited it and she decided renting it out to me would be good for both of us. I’ve been here a couple of years now.”

“I’m sorry about your aunt.”

“Thanks. The doctor said she died in her sleep so she didn’t suffer.”

Luke arrived next to me carrying his ball.

“Why don’t you hop over the fence,” I said. “It’s quicker than going all the way round.”

Luke looked at his mum for confirmation and she nodded. He scrambled over the fence and resumed his almost comical attempts to kick his football around.

“As you can see, my garden priority is low maintenance so there’s nothing here of any value. I’ve told Luke he can come over the fence any time to get his ball back.”

“That’s not the way we’ve brought him up. He really ought to ask permission first.”

“I sometimes work from home. He’d be doing me a favour by retrieving his ball without disturbing me.”

“Well, if you’re sure...”

“Luke seems well-brought up and responsible enough not to abuse the privilege.”

“Becky and I are proud of him, but sometimes we worry he might be missing out by not having a male role-model as a parent.”

“I’m sure I wouldn’t be an adequate role-model, but if he has any problems he wants to share with me for a second opinion, I’d be happy to listen.”

“Thanks. Where do you work?”

I told her the name of my company. “I’m a junior forensic accountant. When an audit hits a discrepancy that’s not readily explainable, they call us in to dig deeper. It’s mostly looking at spreadsheets and following money trails.”

“Becky will be working at the same place. She’s a management consultant. She wasn’t getting the recognition she deserved in her old job and when she put in an application, your lot jumped at her. Apparently they’re short of people with experience of sorting out small companies.”

“Ah, the other lot,” I laughed. “We’re supposed to maintain Chinese walls between the consultancy and accountancy divisions, but I’m sure we’ll run into each other from time to time. Do you work?”

“Yes, I’m a midwife. There’s always a shortage of midwives so there was no problem getting a transfer to the maternity unit at the General Hospital. As the new recruit, I’ll be getting a lot of shifts at unsocial hours to start with but that’s fine because it means I’ll be around when Luke gets home from school until he’s settled in.”

We chatted a little while longer, then mutually decided the conversation had run its course and we had more important things to be doing.

Over the next few days, I saw Luke hop over the fence to get his ball a couple of times. I waved at him to let him know I’d seen him and reassure him it was fine.

I met Becky in the garden before I encountered her at work. I was giving my grass its monthly haircut when I spotted her on the other side of the fence, trying to miraculously resurrect some of the plants damaged by Luke and his football. I shut off the electric motor and went over to introduce myself.

If Laura was the girlie lesbian, Becky was the butch one. She had a stockier figure and a rather square face but she was still quite attractive; another woman I wouldn’t kick out of bed. I was relieved to find that she was as friendly and approachable as Laura, and not at all threatened by my gender. On the contrary, she said she was pleased to be living next to someone so open-minded about their situation.

I first encountered Becky at work a couple of weeks after she had started. The campus hosted several on-site restaurants, but only one was for employees. Normally I preferred to eat in one of the others, where I might overhear conversations with customers: knowledge is power, however it is acquired. But after an exasperating morning trying to work with a customer who wanted us to solve his problems but without offering any co-operation, I’d had enough of customers for one day so I chose to eat in the employee-only restaurant.

Seeing Becky eating alone, I asked whether I might join her and she readily agreed. We were rather stuck for topics of conversation because we had customers in common and we couldn’t discuss them for fear of breaching the Chinese walls rules. So I asked how she and Laura were settling in.

“Laura’s fine. She fitted in no problem and her colleagues treat her as though she’s been there years. I’m finding it a bit more challenging. The work itself is okay, but there’s so much more bureaucracy at a large company.”

“Tell me about it. I reckon one day we’ll have to fill in permission slips just to visit the toilets.”

Becky laughed her agreement.

“What about Luke?” I asked. “Does he like his new school?”

“He’s at a difficult age. He says everything’s fine, but I’m not sure he’d tell us even if he were having problems.” Then something crossed her mind and she looked hopefully at me. “Would you mind having a chat with him? He might open up to you.”

“Well, I’m not sure he’d appreciate another adult getting on his case, but if I get the chance I’ll try to bring it up. But I rarely see him these days.”

“I think that’s the result of being at a new school. They teach a different curriculum so he’s got a lot of catching up to do.”

We didn’t have a lot more to chat about so we finished our meals mainly in silence. As soon as I got back to my office, I was teased mercilessly about consorting with the enemy and I presume Becky got the same treatment.

A couple of weeks went past and I didn’t get a chance to speak to Luke, although I said ‘hi’ to Laura and Becky when I saw them in the garden. Then, one evening when I was using my toilet, I noticed a blueish glow coming from the direction of the house on the main road. Intrigued, I fetched a footstool and used it so I could look out of the opener at the top of the frosted window.

I immediately alighted from the footstool, switched off the light so nobody could see me, dug out a pair of binoculars then climbed back on the footstool. With the aid of the binoculars, I was able to confirm what I thought I’d seen. The bedroom had obviously been assigned to Luke. He was sitting at his computer with his cock out, gently rubbing it as he watched porn.

I’d heard the term ‘beautiful’ to describe cocks before but I’d never really bought it. In much of the porn I’d watched, the cocks were short, had strange bends in them or discoloured patches of skin. And the rest always seemed angry to me, the way their prominent veins stood out. Even my own matched the latter description when it was hard. But Luke’s cock really did justify the term ‘beautiful’. Unlike my own, Luke’s cock was circumcised, and it stood erect and proud. It wasn’t fully grown, being perhaps four to four and a half inches in length, and was in keeping with Luke’s slender build.

Luke didn’t seem particular about the sort of porn he was watching; mostly heterosexual, some lesbian, some gay, some gangbangs, even occasional bestiality. That’s when I realised he wasn’t benefiting from having liberal parents: even they wouldn’t have condoned him watching something illegal. And the first seed of a dastardly idea was born in my mind. I must have watched Luke masturbating himself for well over an hour, and in that time he came at least four times. And his cock never seemed to get truly soft.

I visit the toilet a lot in the following evenings, and found a regular pattern. Luke liked his sessions two or three times a week, always around the same time.

I wasn’t a computer expert by any means, but I knew a bit more than the basics. I bought a new computer with a huge hard-drive, and a high quality webcam with a top-of-the-range zoom. I set up the webcam in my toilet window so that, when activated, I could watch it on my monitor while it recorded to the hard-drive. It was better than I had hoped. I was able to see the porn Luke was watching almost as clearly as he could and, with the zoom fully activated, I had a better view of his beautiful cock than he did.

When I had enough video for my purposes, I extracted a short clip of Luke cumming while watching a particularly gratuitous bestiality video and sent it to my phone. By way of further preparation, I stocked up with condoms. Mine were easy, my cock was average in size and I could buy them just about anywhere. But you can’t exactly go into a pharmacy and buy child-sized condoms. In the end I bought some over the internet where condoms were sold by length and girth, making an educated guess at Luke’s sizes. Now all I needed was an opportunity.

By pure luck, when Luke’s school was on its half-term break, the building where I worked was hit by an outbreak of Legionnaires Disease. The building was closed for a week for remedial work, with senior staff being relocated elsewhere on campus and junior staff like myself being told to work from home unless we needed to attend any meetings. Becky actually contacted me and asked me to keep an eye on Luke while I was home because both she and Laura had to work that week. They had decided Luke was old enough not to need a babysitter but they appreciated someone being around in case of emergencies.

The next morning Luke was out with his football, still utterly inept. And sure enough, the ball soon ended up I my garden. When Luke hopped over the fence to retrieve it, I pounced.

“Hello Luke,” I said from where I had been hiding, making him jump.

“Hi, Sir. I was just getting my ball back.”

“That’s fine. I’d just like to talk to you about something. Would you mind coming inside? I’ve got something to show you.”

“Um, okay,” said Luke. He obviously wasn’t too happy about it, but his politeness and willingness to obey an adult won out.

Once we were indoors, I took out my phone and played the video clip. Luke went white as a sheet, and looked as though he might faint.

“Since bestiality is illegal, I guess your parents don’t know you watch this sort of thing.”

“Please don’t tell them,” begged Luke.

“There’s no need to tell them if we can come to some sort of arrangement to our mutual benefit.”

“You can have my allowance. It’s not much but it’s all I’ve got.”

“I’m not interested in money Luke. First of all, I want you to continue as you are now, masturbating to porn with your curtains undrawn.”

Luke thought for a while. “I guess I can do that, so long as my parents don’t catch me.”

“And second, I want the use of your cock.”

Luke seemed to go even paler. “I’m not gay.”

 
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