Sunday, 15 January 2023

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.


No comments:

Post a Comment