Daniel

I had just left university, and in a job I despised, when I first met Daniel. I walked down the hill from my house to meet him at his car. Our conversation flowed easily. He was a man I hoped would strip me and spank my bare bottom. He was my first spanking partner.

I began fantasising about spanking play when I first got a pornographic magazine. Among the usual thirty-something women with ample curves and pretty faces, dressed up as teenagers, was a picture of a man playfully smacking a girl over his knee. She had her back arched to make sure the reader had an uninhibited view of all her charms, and her top was hitched over her bare, milky-white breasts. It excited me more than the others. But just as much as I wanted to be the man, with a sexy wriggling-but-willing girl laid over his lap, to do with as he pleased, I also wanted to be the one ceding control.

Luckily, the internet isn't short of outlets for unusual desires, and I soon found pictures of frowning, experienced-looking women in pencil skirts and reading glasses, spanking their chubby-looking husbands. But, no girls a generation up on me who could redden my bottom, and perhaps show me a trick or two in the bedroom. A simple beating wouldn’t do it, as in my mind, the spanking always led on to sex.

I found some personal advertisements courtesy of a well-known search engine, but no experienced women looking for a younger man to have some fun with. Latex dominatrices aplenty, but welts aren’t for me. Queuing up behind balding old bankers and circuit-judges isn't my inclination either.

I wanted a telling-off from a knowing vixen who then unzipped and stripped me naked, told me how vile I was for nursing a blood-engorged penis, set me over her lap and spanked me till I was on the edge of exploding with sexual urge. Then I wanted to be indulged in some comfortable, uninhibited screwing. None of the uneasiness and embarrassment of a younger woman, but seasoned, fun-filled fucking with a woman who knew herself and wanted entertaining.

There were none.

Well, what about a man?

By this time, I had been communicating for some time with various spanking devotees on a number of chat rooms. Some were submissive, some the more dominant type. All were a good decade my senior and most old enough to be my parents. I had talked with some of the straight submissives about finding a casual female partner to teach me a lesson. There were so few, and it was an oft-lamented problem, they said. Most of the good ones liked to maintain control of the situation, so a spanking followed by no-holds-barred sex was off the cards. What I wanted would mean dispensing with money.

What about having my bottom beaten by another man, they said? There was no shortage of experienced gay spankers who were always keen to show a youngster a thing or two. But, I'm straight, I said. That would be weird for me.

I let it go for a couple of months. Maybe I could attract a girl to spank? It will surprise no-one that submissive young girls are somewhat hesitant to share their personal details with all and sundry on the internet. The few attractive ones available described themselves as models. That sounded expensive.

I think the trouble is, I've always been a lot dirtier than any girl I've dated, and I've been too Disney-fed and idealistic to make sexual adventurousness one of my top demands in a partner. Looks? Yes. A liberal outlook? Definitely. Brains? Please! Laughs for my awful jokes? Of course. But after that, once we're dating, to someone who knew my tastes it may have looked like I was chasing celibacy. And you can hardly tell if the girl you're seated opposite, at Pizza Express on that stuttering first date, is as good at sucking cock while bending over as she is at smiling sweetly while chuntering on about tennis.

I got chatting to some of the male dominants. What were they looking for? How did they like to play? How much experience did they have with young straight boys? Was I going to end up waking up in a bath full of ice?

Eventually, I found Daniel, and after exchanging a few emails, we began phoning. He was retired and spent his days spanking, being spanked, and doing some volunteering work. He had his own flat on the other side of town, overlooking a famous park, and had been into the spanking scene for 30 years. He liked sex with his partners, but had spanked plenty of straight boys without any penetration, he assured me.

I was a beginner, and he said he'd make sure I had a good time.

Then, we arranged to meet.

I prepared by taking a nice long shower. It was a hot day, so I made sure I was fresh. I washed my hair and face, my arms and torso. I then lathered up by tool and balls, peeling back my foreskin and gently cleaning my purple cockhead. I cleaned by bottom thoroughly, paying particular attention between the cheeks.

I always find this best done by lying down in a bath with a shower, pulling my ankles back and spreading by legs, allowing the water to spray on my boyhole, and then scrubbing away.

When all was smelling sweet, I stayed in the same prostrate position and foamed up my balls and cherry. I shaved, making sure the skin was taught and the shave was close.

I don't have too much hair between my legs, but I always feel cleaner and fresher when it's stripped away, and a part of me wanted to impress and arouse my new senior friend.

I moisturised from my hole to the top of my penis and sprinkled aftershave on my balls. I then pulled on some tight-fitting trunk-style underpants, my best jeans and a long-sleeve black shirt, and began to stroll down the hill.

I found his car. ``Daniel?”

``Yes, good to meet you. Hop in, let's go.''

He was dressed in jeans, with smart black leather brogues and a cream short-sleeve shirt worn open-necked. His skin was flecked with age, and he had rough but fleshy palms as we shook hands. He had splashed himself with a musky cologne. We chatted generally about what a nice day it was, before moving on quite abruptly into talk about the scene.

``So this will be your first time? Well, there's quite a lively scene here. If you enjoy yourself, perhaps I can introduce you to a few people.

``Well, yes, I suppose, I...''

``Ha! Sorry, I didn't mean to get ahead of myself. It's just you're a good-looking lad, I can tell that already, and so I'm sure you'd be popular. Anyway, let's talk about today. You said on the phone you'd like a gentle introduction. Some hand action, over my lap, on your bare bottom,'' he said with a smile, as we drove through the city streets.

It felt new and exciting. The couples and groups we passed on the pavement couldn't have guessed what we were about to get up to. But Daniel could tell I was nervous, I think, which I certainly was. I'm normally the talker among my friends, but it was he who kept the chat going, moving effortlessly from how lovely the park was today, to whether I'd be comfortable undressing myself or being undressed, to what sports I liked, to what sexual idiosyncrasies he enjoyed himself. He, too, liked to be spanked, but I wouldn't be expected to do anything like that to him today.

He asked if I had a girlfriend, and didn't draw breath when I answered that I had. Ginny is a delicious southern belle with hazelnut hair and hand-filling tear-drop breasts. Perhaps I'll talk about her unusual tastes another time.

We reached his flat, and I was casually escorted inside, as he assured me his neighbours knew about his lifestyle and wouldn't complain about ``any noise.'' The anxiousness filling my gut was now splitting in two, it's twin becoming vague arousal.

I followed him up the stairs after taking off my shoes and socks – there's nothing more horrible than being trouser-less, yet be-socked – and we both entered his bedroom. On his double-bed was a towel on which were arranged an impressive array of bum-beating instruments. A leather tawse, a switch, a square paddle made from a pale-looking wood, various thin canes, but none of the fear-inducing, welt-leaving headmaster types. We'd agreed to start gentle. Shafts of light fell through a large, wide window, and a breeze made the leaves on the trees outside whisper.

The bedroom was large enough for two people to walk around the bed and to accommodate a wardrobe and dresser, on which were a digital camera, an impressive pink dildo and some lube. He also had a spanking frame and an armless dining chair.

``What do you think of my toys?'

I merely smiled back. I noticed at this point, Daniel was a good half-head shorter than I, but his poise and bolt-straight posture melted the difference away. He had kind, grey eyes and a smattering of grey hair, which was thinner on the top and brushed to the side. He sat on the chair and beckoned me to sit on his lap, which I gingerly did.

``So, how are you feeling? Ready to start? Do you have any questions, or shall I begin? We're not role-playing, so all you need do is say `stop' and that's exactly what will happen. After our fun, I've got some cream for your bottom and we can have a beer together.''

``Sounds good. Let's start.''

He eased me up, and guided me round to stand in front of him.

``Let's have these off, please,'' he said, tugging at my trousers at the knees. We'd agreed I'd strip myself as it would afford me more of a sense of control, which might be best for a first-timer, he had said. I unbuckled my belt, unzipped my flies and stepped out of my jeans, which he took and threw to the back of the bed. He looked at me and smiled, searching my eyes to see if losing my trousers had startled me.

``Hands on your head, now,'' he said, again, searching my face. ``Let's see what we have.'' He turned me round in a circle, gently slipping his fingers into the waistband of my underwear and pulling it higher, so that my exact contours could be admired.

``Hmmm, perhaps a big boy?'' he teased, garnering a smile from me.

He turned me more, keeping my pants tight, so that my back was to him. ``And a nice firm bottom!' he added, sliding his thumbs deep between the cheeks and giving them a pinch.

``Ow!'' I squeaked, more girlishly than I intended. He then eased me over his lap and began arranging me to his liking, so that my bottom was in the middle. The chair was high enough to make sure my face still cleared the floor by a good foot, as I am quite tall.

Rubbing my bottom with his right hand and smoothing my hair with his left, he said ``Let's get you warmed up, then.''

He began slapping my cloth-covered flesh, reigning down blows no harder than a back-slap for a friend. After each group of volleys, he would rub my bottom round and round, and after each over of blows, he'd either peel back the legs of my underwear, to see how the warm-up was working, or slip a finger between my legs, followed by an apology.

He acted like it was a mistake, but I knew what he was up to. He wanted to see if his light slaps and bottom-rubbing was having the desired effect. After minutes of this, it must have been obvious it was, and I had to part my legs somewhat to get comfortable.

I felt his slaps come down harder and harder and a pulsing, stinging sensation began after several dozen, after which he helped me up, with quite the hot rear; and, as I realised only when his eyes met it, a semi-erection.

``Warmed up indeed!' he said, his eyes fixed on my cock. I was embarrassed, and suddenly very aware of the fact I was a supposedly straight man with an erection at the touch of a gent who was of my grandfather's generation.

The worry didn't last as he peeled down my underpants, clearly judging my reaction as my yielding to him. ``You are a big boy,'' he said, allowing my cock, which was now half-way to erect and lazily pointing at his lap, to lie on his open hand.

With his middle finger grazing my testicles, the head sat on his wrist, peeking half-out from its fleshy home. I gasped as he touched me with his rough skin, but before the gasp was fully out, he had slipped me into his mouth and sucked hard from halfway up the shaft to the tip, letting my cock free with a smack of his lips.

My head rolled back involuntarily. ``That was a surprise,'' I managed.

``Yum,'' the wily fox replied, his voice worn and rough with age. He had me now. My cock had been in his mouth and I had enjoyed it. The spell was broken and the nerves were gone.

Back over his knee I went, and he stroked my legs as he slipped his left hand round my waist and under, looping his forefinger and thumb round the base of my penis, which had now begun to throb. His hands explored my cheeks in between slaps. His left hand made sure my legs were parted wider than I'd have had them naturally, and by the end, between the spanking and touching, there was no part of of my bottom he hadn't pinkened, and no part of my body he hadn't seen or touched from my waist to my knees.

The slaps were hurting now, wonderfully so, and the mix of tender touch and spiteful pain were weaving their magic on my nerve endings. Daniel's grip meant each slap led to pain mixed with a sexual thrust, and the build-up on my hot, red bottom, meant the blows' hurt was manifesting itself in little whimpers.

After as much time as the last round of slaps, he helped me up again, this time sporting a full-blown veiny hardon, pointing straight at him.

He must have thought he's overstepped his mark last time, or perhaps it was part of the torture, but he left my cock alone and very gently ran his fingers along my thighs.

``Now, let's try out the horse,'' he said. He motioned me over to the room's centrepiece, which was like a long, inverted V, or two square frames joined at the top. It was made of a golden-coloured wood, with straps to secure hands and feet at the tips of each V. Being strapped in would have meant your bottom in the air, and your hands and feet spread, and on the floor.

Daniel had been itching at his trouser area in a way that vaguely concerned me since we entered the house. At first I assumed he was merely uncomfortable in his clothes. As I bent over the horse, he showed me the problem.

As he went over to the bed to select an instrument, he unzipped his trousers, and wrestled out his dick and balls, which were collared with a cockring of silver metal. I don't know what I expected from the dick of an older man. Perhaps something small and wrinkled. His penis was about the length and size of a jumbo marker pen, and a darker shade than his other skin. It had none of the marks of age, and his flesh-coloured head – not the purple of my younger meat – was just visible behind his foreskin. It was a cock I'd be proud of too, and it was clearly filling with hot, horny blood.

I was at once worried and also oddly pleased. The nerves of the car journey returned, and the feeling I shouldn't really be there, and that this was all a bit too quick, and had I given him some suggestion he could fuck me? A much smaller and less nervous part of me was pleased at least a man's cock doesn't age.

``That's better. Don't worry, you don't have to touch this. It was hurting and I'd also like you to see it, as I've seen yours and we should be comfortable with each other.'' He peeled back his foreskin ``It's there if you want it, since I've had a taste of yours! You didn't mind that, did you? It smelled sweet and I want you to enjoy yourself. Perhaps I moved too soon?''

``I didn't mind, but let's work slowly,'' I said sheepishly. I was now very aware how vulnerable I was. The frame of the horse pressed against my cock, pushing my balls back and forcing me to spread my legs wider than my shoulders. My hole was on show, I was sure of that.

``Let's get some cream on that hot bottom, shall we? We don't want it too dry or it will really hurt.''

He opened a tub of moisturiser and scooped out a palmful before rubbing it into my cheeks. It was icy cold, and I bucked a little. He smoothed it over from cheek to cheek, rubbing deeper and deeper until he was fingers were reaching deep between. Without thinking, I let out a little moan.

``Back to work!'' he said. Next was the switch, a bundle of broom wood. He slapped with a flick of the wrist, applying a different flavour of pain. Hand-slaps rise within the body, sending a wave of sensation to the brain moments after the blow. The switch is much more immediate and sharp, but fleeting. The pain is worse, but gone as soon as it arrives.

I squealed and writhed. ``Okay?'' he said. I nodded.

On to the tawse, a short strap of leather split down the middle. It bites the flesh and is rougher on the bottom. As the lashes came down, not harshly, but hard, I suddenly felt uncomfortable. The pain felt wrong and my cock began to empty.

``Stop,'' I said. Firmly but without panic. He did, immediately, and helped me up. My mind was in a spin. My own fault, I should have stopped it earlier. My bottom would have been warmed and I'd have been talked into a handjob and perhaps a fingering to finish the day.

Daniel looked worried. ``Are you okay?''

``Fine,'' I managed. ``Just had enough.''

``He flashed a glance at my behind. ``You've done very well for a first-timer,'' he tried to assure me. My cheeks were now burning. No bruises or anything worse, but more than I'd intended.

``Would you like to come off?'' he asked, perhaps hoping that would take my mind off the pain. I'd lost the mood and my dick was retreating.

We talked the spanking through, and I told him I should have stopped him earlier. He looked guilty. ``I should have remembered you were a spanking virgin. I should have halted it,'' he said.

``Trust is pivotal. Let me put some more cream on?''

I bent over the horse and let him rub more of the cold, soothing cream into my bottom. It was a welcome relief from the furnace Daniel had made it earlier, and his touch, now gentle, began the stirrings it had before. My limp dick filled again, and I reacted to his touch by spreading my legs.

``You want err..?'' he said. I nodded. His experienced hands began smoothing the cream into my cock. He then began to milk me, still stroking in more and more cream with his free hand.

I began to buck gently in sympathy. The horse wasn't the most comfortable place to be tossed off, but its padding meant I could join in the fun a little. As the last of the cream was smoothed in, I felt a wetness on my balls as his breath betrayed him against my skin. He licked boldly from sack to anal pucker with the flat of his tongue. It was good. It was my first rimming, and after the quality of his tonguework, I made sure it wasn't my last. Ginny, who is worth another story, was quickly taught what to do.

Daniel hungrily ate my boypussy from behind while his hand pumped away. He had lost me before, but he had me again. His bristly face tickled my tender flesh and I came hard on the floor, gripping the wood of the horse so hard I left nailmarks.

He cleaned the tip on my penis gently with a handkerchief and gave it a kiss. ``Better?''

``Yes,'' I gasped. I dressed..

But I left with my head refusing to process what had happened, and the more basic and unsophisticated feeling of shame overrode all the fun and excitement I'd felt. It took me a year to see him again and it wasn't quite the same. He was just as talented, but I felt I had ruined our last session by letting him go at me too hard and for too long.

I often look back and regret not developing my relationship with Daniel. I wonder what would have happened if we had met again, soon after. I think I'd have become a lot more comfortable with my body and enjoying it, and I think I could have developed my bisexual side better. In hindsight, I think he would have been a good mentor and that eventually I could have given myself to him. He taught me a lot about touch and pain and trust and how the three can be so enjoyable.