Gone Pegging, Part Two

Back for some more pegging filth to celebrate International Fetish Day with me, huh? Well, if you are sitting comfortably, let's get into it!

Last we left off at the conclusion of Part One, I'd just drifted off to sleep after guiding a pegging newbie through his very first anal adventures.

I couldn't possibly say how long I slumbered in this random bed. All I know is that I was abruptly jolted awake again by something touching my leg. You see, I have a thing about personal space, so I'm very sensitive to unwanted contact. If I'm in the comfort of my own home, wrapped in the arms of a loved one, it is no problem at all. But when I'm in unfamiliar surroundings, I will generally quickly wake when my body senses any presences in close proximity to me.

As I groggily rubbed my eyes to get a better idea of who had disturbed me, I beheld a stranger lying asleep next to me, completely bare about from his boxers.

Slightly panicked by this and what it meant, I felt it best to hastily make my exit as quietly as possible. That is sometimes easier said than done when you need to get clothed first. And something that I clearly failed in on this occasion.

I had barely slipped my undergarments back on when I heard a voice behind me enquired, "Why are you in such a rush to leave?".

My eyes went wide with panic as my mind fumbled to formulate a very quick escape plan.

"Don't worry, I'm not mad.", he continued. "It's not everyday that you find such a beautiful lady sound asleep in my bed. I enjoyed watching you sleep peacefully before I fell asleep myself.".

OK, so it was the party's host and not just some random who had climbed into bed with me for a creepy grope or fondle. Things were starting to fall into place and I felt some relief.

"I'm so sorry, I didn't realise it was your bed. I'll make it up to you if I've caused a problem, I promise. Please don't be mad", I spurted out at him.

He replied, "I already told you it's OK. It was a nice treat to see you lying there so peacefully."

"But your sheets! They are stained from what I got up to! I insist, I must make it right somehow. Just tell me how to make it up to you."

He sighed. "I told you, there's really no need to be sorry". Then, after a pause, "But... if you really won't take no for an answer, perhaps you could put that strappy back on and let me lick it clean from whatever naughtiness you got up to earlier tonight".

Unsure whether to be excited at the prospect of being able to further explore my pegging fantasies or nervous about what else he might have instore for me, I quickly slipped out of my underwear and, in its place, slipped back into my strap-on.

Nervously, I perched on the edge of the bed as my host approached me with a lustful look in his eyes. I needn't have worried though. His lust was centred squarely on the toy strapped between my legs. 

A trail of saliva dripped from his lips onto the head of the cock. As it began running down the shaft of my toy, his tongue swirled around my cock, spreading the moistness over its whole surface.

Then, without a moment's warning, he swallowed it. The whole cock! Right down to the base. This was no beginner that I was dealing with this time. This guy was obviously well-versed in the art of taking cock. But what else would you expect from the host of a pegging party? And, unlike my previous partner, he was definitely an older gentleman so clearly had plenty of experience under his belt.

His face pressed against my tummy as he held my cock in his throat, he tapped his hand on the back of his head. Was this the universal symbol for 'hold my head down'? I assumed so and obliged by holding him down with both of my hands.

Saliva oozed from between his lips and my cock as he coughed and sputtered. I held firm and didn't let him come up for air.

Then his body jolted abruptly as he tried to suppress his gag reflex. He wriggled and squirmed, his head trying to push upwards to escape my hold. I still did not let him. Only when he tapped his hand on my thigh, did I release my grasp on him.

Worried that I had maybe gone too far, I awaited his reaction as he came up gasping for air. But, far from being angry, he wanted more.

"Would you prefer it if I fucked you mouth?", I cautiously enquired.

"Yes! Please do that!". A more enthusiastic response than I ever could have imagined.

My host climbed onto the bed beside me patiently waiting with mouth open-wide. There was a look in eyes. Something like "please fuck me now, I'm begging you". It was thrilling to see and I couldn't resist granting his unspoken wish.

The phallic appendage strapped to my crotch slammed down his throat as I violently thrust my hips towards his face. As I pulled it back out, I gave him just enough time to beg for it again before I impaled him once more with it.

And so we continued in a cycle of him begging and then demanding more of my fake cock, with me then gleefully shoving it down his throat. All apprehension about how this may go had long since evaporated. I was completely lost in the depravity of our carnal acts.

What's more, every time I thrust into him, I could see his hard, throbbing cock swing backwards and forth between his legs as he recoiled from the force of my mouthfucking. It was a sight to behold. The thought of taking it inside me was making me so wet. My own juices now mingled with all of his slobber and drool that was dribbling down across my pussy lips.

"Let's suck each other", I proposed. He liked that suggestion very much.

In a rare moment of dominance so far, he shoved me on to my back and pounced on top. Straddling my face, he lined up his cock with my mouth and waited for me to open up. The instant I did so, he slid it all the way in until I could feel it against the back of my throat. It was meaty as fuck and I could only just about take it.

Some relief then he dived forwards to resume sucking my strap-on. As he did so, his rear end cantilevered up, forcing his cock to withdraw from being quite so far down my throat. It was now perfectly placed for me to slurp on it. There was just about enough freedom between the bed and the base of his cock for me to move up and down along it with my lips.

It was  a surreal experience though. I could hear him gagging and slurping down between my legs. I could feel the motion of his body lifting and then pressing down against me as his head bobbed. But I could feel nothing down . It was thrilling yet somewhat hollow. 

Maybe it was just coincidence, or maybe the wetness of my pussy gave him a hint that I craved more. Without pausing from whatever he was doing with that fake cock, he slipped a pair of fingers inside me. Rarely, have I ever taken anything being inserted inside me with such little resistance. I was not only ready for this, but yearning for it.

I thanked him by returning the favour. My middle finger running round the rim of his anus and then gently pushing its way inside. Just like my pussy, there was no resistance. It came as a shock to me in fact. I've never before encountered an ass so willing to accept foreign objects. Definitely experienced, this one.

His response to my finger was completely unintelligible, his mouth too full of cock to be able to properly form words, but I could tell that he approved. 

I don't know what came over me next but, without even thinking about it, I hooked one of my legs over the back of his head and pushed it down. Every time he would try to come back up again, I would force him back down again, no matter how much he resisted or struggled against me.

Eventually, I came to my senses and let him come up for a breather. Instead of chiding me for my aggression, he begged me to fuck his ass. It seemed like being dominated like that had only made him more aroused.

"Please, fuck me now! I want you inside me so badly.", he cried out. "If you keep sucking me like that, I'll cum in your mouth and I don't want that to happen. Not yet. Not until you've fucked me."

Because I can be devilishly wicked when in this sort of lust-filled mood, I made him an offer that I was sure he could not refuse.

"How about we play a game? If you can take all four of my fingers. I'll fuck you in the ass, just like you want. But if you can't... you have to fuck my ass and then cum inside me instead."

"I know I can do it!", he retorted. "Probably your thumb as well. I bet I can take your whole fist!"

His confidence was impressive. He continued, "I've already sucked and fucked one strap-on today. My friend loves fucking me with hers and she loosened me up nicely earlier".

The game was agreed then. All that was left was to decided which of our asses was going to get fucked.

I quickly withdrew my one, solitary finger from his ass and prepared to see how many I could get in. 

Giving them all a good lick, I started with 2 fingers; adding my index finger to my middle finger. Again, they both slipped right on in there without any trouble at all. Contorting my hand, I then carefully squeezed my ring finger in as well. That was not a problem either.

"See, I can easily take them all!", he pridefully boasted.

Before he could even finish speaking those words, my pinky finger had joined the others inside him. 

"OK, you win!", I declared. "Get off me and prepare for your ass mine to be mine!"

He obediently did as instructed. His eyes wide with excitement as he looked back over his shoulder to watch me insert into him. An insertion that, not surprisingly, was very easy indeed. His gaping ass welcomed my fake cock with open arms.

Regardless, I took it easy on him to begin with. Teasingly, sliding it just the head of my toy in and out. Stretching him open just a little bit and then letting him relax. He wanted more though.

"More, more, more! I want it all!", he cried.

So I shoved it all the way in, only stopping when my thighs clapped against him and I could push no more. 

"Yes! More like that! I want it!"

My god, he was insatiable. There was no begging now. Just demands and orders to give him my cock hard and deep in his greedy ass.

Well, if he wanted more, that was exactly what I was going to give him. One of my hands reached round and grabbed the shaft of his cock, jerking it furiously. It throbbed and twitched in my grasp but he held the urge to cum back... for now.

But still he demanded more! I was at a loss for what else I could do. The limits of my pegging experience had been reached and exposed. I had but one idea.

Reluctantly, I released his cock from my grasp and pushed myself up from my knees to my feet. As I did so, I pushed him forward onto all fours and squatted over his rear. Carefully, I lined my cock up with his anus and then drove it deep inside.

Hard, deep thrusts into him, followed by slow, almost lingering, withdrawals. Not a millimetre of my strap-on's shaft was being wasted now, He was literally taking the whole thing. He cried out with approval again and again. 

"Fuck, if you keep doing that, you'll make me cum all over my bed!"

I slowed for a moment. Still giving him the whole length of my toy but now inserting it as slowly as I had been pulling out.

"Where would you like to cum?", I asked. "I'm still making up for using and staining your bed so I'll let you cum wherever you want."

 

Secretly, I hoped he would say my ass. It would have been the perfect way to finish off our filthy fucking. And I still wanted to feel what that yummy cock would feel like inside me.

He had other ideas though.

"Just keep fucking me. Let me cum while my cock hangs free. Make me cum just from fucking my ass. I'm so close. I know you can do it!"

Well, any disappointment I may have had was soon displaced by a determination to prove him right. There could be no holding back now. Just hard fucking as I railed his as over and over with my fake cock. I am quite sure that never before have I been reduced to such animalistic fucking. I was like a woman possessed.

I slammed him again and again, then he began to buckle under my weight. He quivered and moaned. Yes, I'd done it!

"Cumming! I'm cumming!"

The fucking continued as he juddered and grunted. Then he slumped to the bed, sliding off the end of my cock as I still tried to furiously pound away.

Looking down at my handiwork, I could see a large damp patch on the bed where he had drained his balls. A few rogue drops of creamy cum also speckled my boots. No doubt some spray as his swinging cock discharged everywhere.

Our eyes met for a moment and simultaneously broke out into giggles. The realisation of just how ridiculous our filthy fucking must have been hitting us at exactly the same time.

"Well, I think you have definitely made up for any inconvenience caused by occupying my bed", he joked.

I smiled, "I think I need to give you cock a good clean and then I'll be satisfied that I'm in the clear."

He wasn't about to argue with that as my tongue began stroking up and down his shaft. He was still very sensitive and was easily sent into a quiver if I touched him too heavily. His soft moaning was intoxicating to hear. I could not resist rubbing my clit while sensually licking him clean. 

"Oh, by the way. that friend I mentioned earlier... I also fucked her in the pussy and ass too", he remarked with more than a glint of satisfaction in his eyes.

"I should definitely give you a good clean then. It's very important to keep clean, you know. And why don't you tell me more about what you got up to earlier?"

My lips wrapped around his cock again but softer than before when he had been on top of me before. The occasional groan would interrupt his detailed description of his earlier sex. It sounded so delightful and got me even more turned on. I now had 2 fingers deep in my wet cunt, squelching each time I gave myself a little come hither mention.

"You know, I think you have gone above and beyond making things right by now. It would be my pleasure to help you cum too. If you would like that?" He smiled down at me as he pulled me to my feet and began fumbling with the buckles on my strap-on's harness. "Come, let's get you out of this and I can finally find out what you really taste like, instead of this fake thing"

As I wriggled free of my instrument of pegging, he laid me on my back, being careful to avoid his puddle of cum on the bedsheets, then lifted my legs over his shoulders. Without hesitation, he dived in and buried his face between my legs. Alternating between sucking on my clit and lapping at wet pussy lips with his tongue, he was driving me wild. 

Meanwhile, my hands busied themselves with my perky boobs. In between cupping and squeezing them in the palms of my hands, my nipples, so hard from my state of arousal, were pinched and flicked and pulled. I cannot describe how much I like having my tits played with whilst my cunt is being stimulated too.

Having had two sexual partners cum today but still to enjoy that bliss myself, my pussy was dripping wet from the excitement of finally getting to take my turn. This wouldn't take long though.

And sure enough, it only took a few minutes of him doing this to me to get me to the edge of cumming.

My inner thighs tightened around his head and my back began to arch up as all of my muscles started to feel tighter and tighter. And then the release of sexual satisfaction hit me. Not so much like a wave but more like a tsunami.

Pussy juice sprayed from between my legs, soaking my host. Clawing at the bedsheets, I quivered uncontrollably. A moan of unrestrained pleasure released from somewhere deep inside me as I threw my head back and let it all out. It had been worth the wait.

With the orgasmic pleasure subsiding and I opened my eyes, I couldn't help myself but let out another laugh. Honestly, the state he was in; his face poking between my legs and absolutely drenched in my juices was hilarious. It tickled me something rotten.

He took it in good humour and we shared a good laugh about it as we snuggled up together for a little bit of post-fucking aftercare and recovery. Of course, the bed was completely soaked now, so my attempt to make up for getting another man's cum stains on his sheets had ended in them being in a much worse state, but he wasn't bothered.

Then, after a brief and rather damp snuggle, I prepared to make my exit once again. This time instead of trying to covertly get dressed and sneak out the door, I was able to casually put my clothes back on and give my host a goodbye kiss on the cheek. 

Something tells me that this might not be the last of his parties I attend though.

Gone Pegging, Part One

So, I should probably start off by apologising. When putting together a list of dates for this years Official LauraTWK 2023 Digital Calendar, I pulled the dates from various different resources and it seems like one of them may have been a little questionable.

I had Fetish Day down for January 15th but, whilst doing to some research for a blog article about fetishes, I found several references to International Fetish Day falling on the 3rd Friday of January, which would be January 20th this year. I'm not sure if these are different days (one being International and the other not) or if the place I got the original date was just wrong.

Either way, by the time that I had discovered this discrepancy, I'd already been busy celebrating Fetish Day in the best way I know possible; with some sexploits!

So I figured that I'd give you half now and half and Friday. That way I'll have covered off both days and you get a double dose of Laura's Sexcapades. I'd call that a win win situation!

I don't think I'm what you would call a fetishist but, after thinking about it for a while, it did occur to me that I like pegging. That's got to be a fetish of sorts, right? And very conveniently, I've recently been seeing a pegging house party that is open quite often. It's almost like it was meant to be!

It was moderately busy when I arrived at the pegging party so I decided to lounge around on one of the beach chairs and wait until I got propositioned by one of the guys there. I waited and I waited and I waited... but nothing.

As is so often the way when I want to have some fun, it seems like simply going to a suitable place and making myself available is not enough. So I decided to be bold! Exploring the inside of the house, I discovered a rather nice bedroom, which would be the perfect place to entice someone into letting me fuck their ass.

I stripped off and prepared my strap-on for action. And then waited for someone to take interest.

This time I was not kept waiting for too long. A young man timidly poked his head round the door and approached. Submissively kneeling before me, he complemented my beauty and the size of the thing between my legs. It was this last comment that really got my interest as it strongly implied that that he had an interest in the same thing as me. 

After politely thanking him for his kind words, I enquired about whether he was into pegging. His response surprised me somewhat but also intrigued me.

He told me that he was only 20 years old and very inexperienced. He then continued by telling me that he very much wanted to try pegging but found it embarrassing to talk about and was ashamed of himself for having such dirty thoughts.

Taken aback by this, I reassured him that there was nothing wrong with wanting to try new things and that he shouldn't be embarrassed by it. Then I made him an offer that perhaps I could help him to try some of these things that he thought were too taboo to discuss with others. 

His eyes light up with excitement. He proclaimed how comforted he was by my words and that yes, he would love to have an older woman guide him on his journey of sexual discovery.

By no means do I consider myself an "old woman" but I suppose in this case there was truth to his words. I mean, I am almost twice his age. Although not the largest age gap to someone I have performed sexual acts with, that honour belongs to a gentleman in his 60s who was 30 years older than me, this would definitely be the largest gap in the other direction to someone younger than me. 

It was actually kind of thrilling to be given such responsibility by him. A responsibility that I would take seriously. So, when he eagerly climbed onto the bed next to me and spread his buttcheeks apart for me to enter, I had to slow him down and explain that we would take it slow and steady to ease him into this new experience.

First, we would just get him used to handling my fake cock as he had never before even touched one, let alone taken one inside him. I also explained the need to get it nice and slippy before attempting any sort of entry into him. 

We started with some light licking before quickly progressing onto sucking the tip. All the time he wanted to do more and more but I tried my best to reign him in and take things steady. Despite that, he was soon begging me to push his head down to help him swallow the whole of my fake cock. 

Bit by bit, my hands applied the pressure required to ease his head down between my legs; my cock disappearing between his lips as it did so. I was impressed that he was able to handle it without gagging. Good going for a first timer.

Embolden by this success, he wanted to move things along quickly. He begged me and implored me to but my cock in his ass. If not his ass, then how about his mouth, he enquired.

I probably shouldn't have but I found this prospect quite tempting and, since he had done so well swallowing my cock now, I saw no harm in giving him a little bit of what he wanted.

Of course, I showed plenty of restraint by holding back from properly fucking his mouth. I gave him just enough that he could feel some sense of achievement and progress, without really testing how well his throat could take me stuffing my cock down it.

Once again, this only served to build his enthusiasm to try more. Again, I had to slow him down. Sure, my cock was nicely lubed up from me shoving it into his mouth, but his tight virgin asshole would not simply accept something of this size without a little preparation. 

If he wanted to take my cock, first he would have to take a finger, and then maybe two. If he could take those, only then would we think about stretching him open with my strap-on.

Disappointment was etched on his face that I would have to wait a little longer to realise his darkest fantasy, but he was also appreciative of the good care I was taking of him.

As my tongue started circling around his tight anus, he exclaimed that it was the first time that he had ever been touched there but he liked it very much. His hardening cock swaying in front of my eyes confirmed how aroused he was by it. 

Then my tongue pushed inside slightly. His semi-hard cock stiffened instantly as he stifled to suppress a loud moan. The moan escalated to a gasp as my index finger gently pressed against his anus. 

Worried that I was going too fast for him, I checked if he was alright. He begged me to keep going. 

Slowly, my finger disappeared into his ass. First up to my first knuckle and then up to my second knuckle. Then another pause to check how he was feeling. It was uncomfortable for him but he was desperate for me to keep going.

I promised him I would but only after rewarding him for being so brave. 

Another gasp as my tongue swirled around on his tight ball sack. Taking his cock in my spare hand, I could feel it twitching as my tongue glided across his skin, introducing him to a type of pleasure that he hand never before known. A subtle stroking action accompanied by ball licking antics.

My finger was still half way into his ass and, the pleasant stimulation of my tongue and other hand on his balls and cock, I used this as a distraction to fully insert my finger into him. There was some resistance but a firm push was sufficient to get it in him.

He looked in discomfort but, again, reassured me that he was enjoying it and wanted more. He wanted another finger. I obliged and inserted a saliva-coated middle finger into him as well. 

It was only now that he had managed to take two fingers that I started to finger fuck him with them. As they slid back and forth, I could feel the resistance gradually decrease as his anus became more accepting of them. This was good progress.

Again, he begged me to fuck him with the toy between my legs. This time I consented on the condition that we would go slow.

It would take more than some spit to get my fake cock inside him. I reached to the night stand and grabbed a bottle of lube that someone had left lying around. Squirting some on my fingers, I ran them around the rim of his butthole and then inserted them one more time. Then a healthy amount in the palm of my hand, I gave my cock a good stroke to smear the lube up and down its full length.

Bending him over onto all fours, I double checked with him whether he was ready for this. Insisting he was, he implored me to fuck him.

The tip of my cock began to put pressure on his anus as I began to ease it in. There was a lot of resistance so I didn't force it. I could also tell that it was uncomfortable for him but he wouldn't let me stop. 

He gasped as his asshole stretched to consume the whole head of my cock and I paused there for a moment.

Once more, I simultaneously rewarded him for his good effort and distracted him from the pain by reaching round and softly stroking his throbbing cock. His gasps and pants turned into moans and groans at my delicate touch on his manhood.

Sensing him to now be a little more relaxed, I resumed easing my fake cock inside him. Little by little the shaft of my toy disappeared inside him until my thighs were pressed up against his body and there was no more to insert.

Craning his neck to look over his shoulder, he beamed with pride at the sight of me being fully inserted inside him. 

Getting carried away again, he demanded that I fuck him hard and deep. Knowing better than him, I did begin to move my hips but only to give him slow, shallow penetration. There would be no hard fucking. Not yet.

He insisted he was ready for it but I would not be rushed into giving it him. Instead, I gradually built up the intensity of my fucking. At times, giving it to him slightly deep but being very carefully not to be too hard. Other times, giving it to him slightly faster but while keeping my thrusts shallow.

Still, he wanted more. More and deeper. Deeper and harder. Harder and faster. Only once I was fully satisfied that he was relaxed enough did I start to give him his wish.

Pulling him upright in front of me, my hips gave sharp but deep thrusts, pushing my cock deep and forcefully inside him. He wailed with pleasure, begging for more and more. It was hard to believe this was his first time doing this as he was taking it like a champ.

The full length of my cock's shaft was now sliding in and out of him. His ass was fucking mine and he was loving every second of it.

Every time I thrust into him, his throbbing cock would swinging back and forth as his hips were pushed forward from the impact of me clapping against his ass. It was too hard to resist. I wanted to touch it again.

There was nothing delicate about my touch this time. Firmly stroking it while I fucked his ass, I could feel his pre-cum seeping out and getting my fingers sticky. It was a thrill! I wanted to furiously beat him off but, this time, I had to restrain myself rather than him. I couldn't make him cum until we had tried one last thing.

Until now, I had been in complete control of him, so his final new experience with me would be to take some of that control for himself. A big step for sure because time and time again he had shown his naivety towards anal play by just wanting to go full steam right away. It had only been my leash that had held him back from going too hard too fast. It was time to take that away though.

He looked slightly worried and unsure as I told him that I wanted him to ride me. Despite his bravado until now, he clearly understood how well I had been taking care of him to protect him from his own over-eagerness. I reassured him that I would still look after him and not let him do anything silly.

Just like earlier, my words put him at ease as he climbed on top of me and gingerly attempted to insert my cock back inside him. It took a few attempts and another helping of lube but we got there eventually. 

His initial movements were awkward and unsure, not quite sure what he should do. But, after a little trial and error, he found a good groove. His hips rocked back and forth as he began humping me. His hard cock slapping against my tummy each time he did so. 

Before long, his movements were becoming more energetic and more exuberant. Soft moans and groans turned into panting and heavy breathing. A wide smile across his face as he fulfilled the fantasy that he had long held but been unable to act on.

And then he began to shake and shudder. He tensed and moaned loudly. 

A hot stream of cum erupted from him quivering cock. As it sprayed across my tummy and tits, another stream fired out across my skin. And then another. He emptied his balls all over me before slowly pulling himself off of my cock and then slumping down beside me.

Taking a moment to compose himself, the realisation of what he had done struck him. He apologised profusely for covering me with his sticky spaff.

Continuing the theme of our encounter, I reassured him that it was OK and that I wasn't mad. He remained sheepish though so I gave him the chance to make it right to me. I instructed him to lick up every drop from my skin and hold it in his mouth. But he mustn't swallow any, no matter what.

Diligently, he did as instructed. For that, he was rewarded with a deep and passionate kiss. His cum passing back and forth between our mouths. As some tried to escape by running down our chins, I swallowed as much as I could. Yummy.

One final kiss, this time a slightly sticky peck on the cheek, and then I sent this very satisfied, and now slightly more experienced, young man on his way.

As for me, I curled up on this oh so comfy bed for a few moments of rest and recovery. Perhaps it was a little too comfy though as my eyes became heavy and I quickly drifted off to sleep.

But you will have to wait until Friday to find out what happened when I awoke.