Toyboy Gets Behind

Toyboy Gets Behind

1986, Yorkshire, England.

Author's note. This is the fourth Toyboy story and follows the timeline from At Home with the Toyboy. It stands alone as an individual story, however. It is not necessary to read the previous three stories first.

*

It had been a hot, hard day at the steelworks and I was glad it was over. My head was pounding and my ears still ringing from the unrelenting thump-thump of the pressing machine. Ear defenders were scarce and rarely used even when available due to the macho attitudes of the workers. I found a seat on the works bus upstairs with a few of my colleagues.

It was raining heavily and the windows were soaked with condensation. There was a heavy, damp smell and a constant, exaggerated swish-swish noise from the antiquated vehicle's windscreen wipers. Despite the fact I didn't smoke, the passive fumes from others felt somewhat relaxing and a welcome change from the hot, dry fumes of the machinery. I was filthy and smelly already, to put my overalls in the wash, have a shower then open a cold beer were the first things I was going to do upon my return home.

The guys were a bawdy bunch. With a pretty, Italian-born, Yorkshire bred girlfriend who was much older than myself, I was a regular target for a good ribbing. The one guy, my friend Tim, was taking the piss out of my hair. I hadn't visited a barber for a while and had let my dark, wavy locks grow longer than normal. "I reckon she grabs your hair and says 'Lick me Ed', then grips you like this," he held an invisible head in both his hands and gyrated his crotch inches away, much to everyone's childish amusement, including mine. He was a little too close to the truth for comfort.

With a squeak of brakes and the familiar thud of a sunken drain, the ageing bus shuddered to a halt. I said a farewell until the early morning and stepped out into the driving September rain. I was alone with my thoughts, which as usual, were about my thirty-seven-year-old lover Millie. At eighteen, I was less than half her age. She claimed my virginity soon after moving into the house next-door to where I lived with my parents. It seemed like a lifetime ago but was only a few months.

She had taught me things about sex that I couldn't have imagined. I got the impression that I was bringing plenty out of her that she had never before explored too. For example, a tantalising, leather-clad, alter-ego who performed a sultry striptease and masturbated with a dildo in front of me just a few nights before.

That night, we had spoken about sex fantasies. She shared with me a tale from the sixties about group sex and free love that her friend had experienced, but such opportunities and experiences had passed Millie by as she was a teenage mother who had spent the last twenty years in two ultimately unsuccessful marriages. There was a lot of wasted time to be made-up for as far as she was concerned and I had a feeling this was going to be done, preferably with me, or without if I was too prudish. I was not prudish, however and would be with her every step of the way to the sexual redemption she sought.

In the street outside my flat was my black 1980 Ford Escort RS2000, which reminded me I still hadn't heard anything from the Ginelli brothers. They had given me the beautiful car as a replacement for the orange car they stole, after the police were looking for evidence against them of stolen vehicle parts. It had turned out my orange Escort was full of that evidence. In a kind of twisted logic, the brothers considered stealing my car as doing me a favour, one which I would need to be returning at some point.

Behind my car, I saw a light blue '79 Ford Fiesta like Millie's. I had given her a key and told her to make herself at home whenever she liked, not particularly expecting her to actually do so. I ascended the two flights of Victorian stairs of the converted, terraced town house into which I had moved just a couple of weeks earlier. My nausea and weariness from the day's work was gone with the thought that she was possibly there waiting for me.

I guessed she wouldn't want to hug me in this state, but after a shower, she would be all mine.

I inserted the key and pushed the flimsy, wooden door. Apart from the usual road noise outside, nothing.

Disappointed, I closed the door and began to unbutton my dirty, rain-soaked overalls for washing. In just my boxers, I placed them in the washing machine and cranked the dial, taking three attempts to stop the blasted thing on programme number six. That was when I noticed it. A red, sparkly handbag next to the cooker. Millie was here.

Switching on the washer, I walked through to the bedroom, hoping she would be there wearing nothing but black lace and a come-hither smile, but nothing. It was a small place, if she wasn't in the bathroom, then she'd been and left her bag.

The bathroom door was closed, but listening through the door, I heard the sound of running water. She was in the shower. With the constant din from the main road outside, I hadn't heard it from the kitchen.

I remembered one of the fantasies we had shared on that drunken night only a few days before. She had a rape fantasy and had instructed me that at any time of my choosing, I was to take her by surprise and do 'whatever I wanted'.

Gently pushing the door, I peered through. My shower was one of those that was added to the wall and utilised the bath for standing in. Through the translucent curtain I saw the hourglass silhouette of my thirty-seven-year-old lover, washing her hair happily. She hadn't seen me. This was that perfect opportunity for her fantasy to be played out. It might've been why she was in my flat. I contemplated for a second while removing my boxers.

She seemed so contented, maybe I was the wrong person for a play-rape, too empathetic. Besides, it seemed a bit clichéd in the shower, a bit too Psycho.

Besides, I had another idea. I crept up to the curtain and peered around. Her naturally tanned back and ass were covered in the river of shampoo that was cascading down as she soaped and massaged her long, dark brown hair. I watched for a few seconds with a hand on my hardening dick as my oblivious woman washed the day from her hair. I had a tantalising side-view of one of her slightly larger than average, pert breasts.

Her soaking ass cheeks shone as the foam found a channel down through the valley in between. That was my target. We had also spoken of anal sex when sharing fantasies a few nights before. Millie confessed she had never done it and thought she may not like it, but could try it someday, "just to have an opinion on the subject."

I stepped into the bath behind her and ran my hands down those generous hips. She didn't flinch, maybe she had heard me, or she smelled my smoky, metallic work-odour.

Turning around, Millie gave me a wet, foamy kiss on the lips that tasted of coconut. I took the shower head and rinsed her hair thoroughly.

"You smell like a man who has worked hard," she said diplomatically, taking the shower head and soaking me, "let me wash you down."

With a soapy sponge, she washed away the workday, using her hands to caress the foam into my body, tantalisingly ignoring my balls and hardened cock. Turning me around she washed my hair in her fruit-scented shampoo and rinsed me down.

Once clean, we kissed long and hard. My hand ran down her body to that fresh, newly pubeless vagina she had revealed to me only days earlier during an erotic dance. She threw her head back with pleasure as my fingers entered the warm, soapy space. She read my mind and turned her back to me readily.

With a freshly-soaped boner, I pushed softly into her ass crack. Gently, I ran my teeth over her neck and shoulders while brushing the head of my cock up and down over her anus. I felt Millie thrust her head back and kiss my neck in that way she would when she let go of that inner passion.

The feel of my dick between her ass cheeks, brushing that hole that had never before been entered gave me the overwhelming desire to complete the deed, here and now.

Millie moaned her approval as I pushed my big, hard boner like an introductory dance against her anus, despite knowing that it wasn't going in without a fight against mother nature.

Kissing down the back of her neck and all the way down her back, I dropped to my knees and parted those beautiful butt cheeks. With my face in between, I was at perfect height to probe with my tongue.

The tip of my tongue licked around the rim of Millie's rear entry, causing her to take a sudden intake of breath. She leaned forward with her hands against the ceramic tiles and pushed her ass out a little further, giving me easier access and unspoken permission. I held her hips as the water landed directly on my head and back. Running my tongue up and down slowly over her anus, she let out a squeal of delight, like a kid who opened a Christmas present and unexpectedly got everything she always wanted in one box.

Millie bent over further, giving me full access to her anus and a beautiful view of her pussy. With soapy fingers, I entered her pussy while licking her butt hole, she started making louder noises. I knew she would scream loudly when she reached orgasm and I wasn't going to stop until she got there.

With a harder push of my tongue, I entered where no man had before gone, probing half an inch or so inside the warm, narrow crevice while my fingers probed deep into the cave next-door. I heard a loud "Oh my fucking god" from my lover whose head was down by the bath taps. I felt she might slip at the angle so propped my knees against her heels for stability. I was way too invested at this point to let a sudden slip injury ruin things.

Using my fingers to rub her clit and penetrate her vagina, I licked and sucked her ass furiously. It was never a position I had contemplated myself being in until this moment, but some force of nature took hold of me and I knew she was going to orgasm right there in the shower, I could hear in her short breaths and quick gasps of "Oh, oh, oh, yes, yes," that she was getting closer.

With my fingers opening her ass as wide as I could, I probed deeply with my tongue. I could hear she was being driven wild with pleasure. "Fuck, yes, oh yes!" she screamed loudly as her body went rigid with an orgasm.

Millie stood up suddenly and stepped out of the bath, leaving me rooted to the spot on my knees. With a naughty smile and a giggle, she looked back at me and ran from the bathroom. I took off after her and saw her naked and dripping wet in the kitchen fumbling in her handbag. Then she ran into the bedroom.

I walked in behind, just in time to see the sight of my lover lying on her front on my bed, squeezing a tube of KY Jelly sex gel onto her fingers. This woman keeps sex lube in her handbag? Applying plenty, she rubbed it deep into her ass crack then stretched her arm out waiting for me. As I got there, she applied a heap more to my hard dick.

This was the moment I had been waiting for. I experienced a feeling in my stomach of sweet anticipation. My heart was pounding. My naked lover was lying flat on the bed before me, her beautiful ass glistening with sex lube begging for me to enter.

I remembered the words of Tim who had spoken of anal sex many times. "Don't expect it to go in without a fight. It may not go in at all," he had said. The pressure was immense. Millie was the one who took the lead so many times, now it was my turn.

"And whatever you do, don't cum inside her ass. It's bad form to cum inside her ass," was the other thing Tim had said. There was a lot to remember. I moved on top, both of us still dripping wet from the shower. Millie greeted me with a twisted neck and a long kiss. I positioned myself over her back and offered my slippery cock to her ass. There was so much gel it was difficult to tell where I was meant to be putting it.

After what seemed like an eternity fumbling, but in reality was probably a few seconds, I found her anus by relaxing and listening to her breaths. With a gentle push from my hips and a raise of hers, it felt like my dick was entering, but when I pushed harder, it slipped away.

I rolled my lover onto her side for better stability and lay on my side behind her, then tried once more. That felt much more comfortable, this time I found the hole easily. Millie guided me in and took a sharp intake of breath. Both our anal virginities were officially gone in that instant.

I was careful not to push too hard, wanting Millie to enjoy this at least as much as I did, hopefully even more. I took my time and listened to her breaths and groans.

Now that I was in, it was time to return to the original position. Millie lay flat on the bed with me still inside her ass. This was a better position for giving her the anal sex she deserved.

Millie's ass raised to greet my dick as I pushed a tiny amount further in with every careful thrust. She was making deep, guttural moans as opposed to the high-pitched wails which I was used to.

I was getting a different feeling to vaginal sex. The narrower avenue down which I was heading gave my cock the sensation of being massaged firmly from every possible angle by someone who had just taken their softened hands out of soapy, hot water. I only hoped Millie was getting the same pleasure from this as it was an avenue I wished to explore again and again.

My dick was three-quarters in and appeared to be as far as it went. I started fucking her ass faster and harder, keeping a close eye and ear on my lover. The harder I fucked her ass, the louder her groans. That borderline between pleasure and pain was a massive turn-on for her, if a big, hard cock in the ass gave her pain, she'd be loving every second of it.

"Pull out," she instructed suddenly and reached for more lube. Smothering my dick with even more, I re-entered, sliding in easily this time. With a few gentle pushes, I was at the point I had just left. This time, I seemed to have an avenue to push further into. I gave a thrust and my whole dick was swallowed.

I stayed in position for a few seconds. Millie gasped and turned her neck to look up at me with a dirty smile and a bite of her bottom lip. I knew that was my green light to really get this show moving.

Balls-deep into the finest ass I had ever seen, Millie's low-pitched moans turned to more familiar, higher pitched wails as I quickened the rate at which I was fucking her. My hips met her ass cheeks with a loud slapping, amplified by our moist skin from the shower.

Millie raised herself up onto her knees to give me even deeper penetration. She looked round to me with a look of sheer lust. "Fuck my ass, fuck me hard!" she commanded. Up on my knees, with a strong grip of one hip, I gave a firm whack of my hand on her ass cheek, then pushed in as far as I could. Millie was bent forward on her knees and elbows. With the warmth of her back-channel enveloping my whole cock, I knew that it was going to absolutely explode when the time came.

As if reading my mind, she looked back once more. "Cum inside me!" she said breathlessly. Normal sex rules never apply with this woman, why should they with anal sex? I thought.

With a grip of her hair, I pulled her body up to meet mine as I pumped hard at her ass. I gave her several kisses on the neck and a caveman instinct hard bite on the shoulder. This sent her over the edge, I felt her body contort and her skin harden into goose bumps as she let out a loud, screaming orgasm. Instinct told me to move my head just as a potentially nose-breaking back-thrust of her head came past my ear. I wasn't going to slow down at this point and took a firm hold of her tits as I fucked her.

Millie's head was still thrown back over my shoulder in ecstasy as my cock penetrated places deep inside which were never before explored in her thirty-seven years. Her body was red with heat and sweat. The wild look of sheer lustful desire on her face was driving me crazy.

Millie planted a huge love-bite on the base of my neck, which was one sensation too far and I felt the tingle in my balls that meant I was going to blow. Every instinct inside me told me to pull out and shoot over her back, but I was under instruction to cum inside her. I fucked her ass harder and passed the point of no return.

As always, Millie sensed this and her screaming became high-pitched once again. She bent forward onto her elbows once again to get the best possible angle. I pushed inside her as far as I could, making the most of the last few seconds of this new-found route to ecstasy. With a caveman-style roar, I shot the full contents of my balls deep inside her ass. Millie gave a loud shriek of delight and wiggled her ass as my love juice entered her back channel.

She started giggling and then laughed joyfully, turning over as I exited her. "Fucking hell, Edward. You really know how to fuck a girl," she said breathlessly and hugged my neck.

Millie stayed with me all week, only going home to change clothes. Our love was growing through sex and experimentation, despite our age difference. It was to be put to the ultimate test just days later.