And holy fuck I’m addicted.
A bit of a long story, so settle in.
I’m a 30M who’s recently started experimenting with pegging. I have a friend who I know has experience with pegging, who’s been breaking me in to it. We have no romantic involvement in our friendship. I’ve just been letting her bend me over at her apartment, and use my back door as she sees fit. Her one condition has been that I only refer to her as “goddess” while we have this arrangement. A fair trade in my mind.
The first handful of times were very tame. Very gentle, slow sessions to get me accustomed to it all. I was new to pegging, so of course I had to make sure I would enjoy the feeling first. Which of course i did.
This latest occasion, however, I felt I was ready for a more, rough experience.
I’ve lurked on pegging subreddits, and I’ve seen some gorgeous, strong women giving other lucky bastards the ride of a lifetime. Long, hard, fast strokes. Taking them to their limits. And dammit I wanted that. I had shared a few posts with her in the weeks leading up to our next session. Her responses were generally “Yup, done that before” or “Thats something I can maybe work with.”
I arrive at her place, and she’s already in her attire for the evening. Matching black lace bra and panties, high heel boots that come up to just above her knees, cherry red lipstick, and a mask that only covered about 1/3 of her face (somewhat like in Phantom of the Opera). My jaw dropped almost into her downstairs neighbor’s living room. She’d worn some saucy outfits in the past, but this was next level. Oh, and I shouldn’t leave out the most important detail. Attached to a black leather harness secured snuggly around her hips, was an 8.5” long, pink dildo that had a noticeable girth to it. At the time, it almost seemed as thick as a soda can.
This was new. In our previous sessions, she had used a 6”, black strap-on that was geared more towards beginners. I had got used to the previous size, so seeing this new dildo was a bit of a shock, but also a welcome challenge. I couldn’t stop staring at it.
“See something you like?” she asked, with a cocky grin across her face.
All I could do in the moment was nod my head. She walked up. In those boots, she stood maybe an inch or two shorter than me. She took her hand and grabbed the waist of my pants, looked me dead in the eye and said “Then how about you show your goddess how much you like it?”
And with that, I was guided back to her room. She told me to undress, and I obeyed. Once I was naked, she put me onto knees in front of her and proceeded to have me suck her ladycock and get it wet. After a few minutes of this, she guided me up, then, with a force that I wasn’t entirely prepared for, she shoved me back onto her bed.
“We’re cutting the foreplay short today. I want to get inside you now” she said, in an almost growl.
She climbed over top of me, grabbed the bottle of lube from her nightstand, and applied some to her fingers. She then quickly worked her hands down my chest, traced her fingers along my abdomen, along the length of my shaft, down to the entrance of my tight backdoor. As she had done before, she teased around the hole before slipping in her middle and ring fingers. Being that this was our fifth or sixth time in the last 4-6 weeks, my asshole had become accustomed to this early foreplay. And she knew this. She slides out her fingers, and I then feel the tip of her dildo pressed against my hole.
“Now, let’s see how this little butt slut handles my big cock” she says as she penetrates me. The girth difference in this cock was immediately noticeable. I let out a small gasp as she pushed deeper into me. Feeling every inch of her thick shaft stretch me out was almost like being reintroduced to pegging all over again.
Once she had pressed herself almost all the way inside me, she began to give short, slow thrusts. Just enough to warm me up to her size. Gradually, she elongates her strokes, but still keeping a slower steady pace. She knows exactly what she’s doing with me, through out this whole process.
After the first few minutes of having that lovely pink cock in me – giving me gentle, deep thrusts – I gave my goddess the look that said I was ready for more. A devious grin crept across her face. She slowly reached her hands around my thighs, and grabbed on to my hips. With great power and control she thrust every inch of her strap-on into me. My eyes literally rolled back into my head as my brain tried to process all the sensations of pleasure it was suddenly receiving. She withdrew at an excruciatingly slow pace. Then she slammed her cock into me again, our hips clapping when they collided. With every thrust, my moans grew a little louder. I was losing myself in the feeling of each and every strong stroke that plunged itself into the depths of me. Thrust after thrust, I was allowing myself to be used as simply a pleasure toy for her.
“I hope you know, this is just the beginning,” her sultry voice filled my ears and sent lightning down my spinal cord.
Before I could even process her words, my legs were pushed back, and my feet were nearly behind my ears. Mind you, I’m not a small man (6’0, 285lbs, muscular build, ex-football player). She locks eye contact with me, and I couldn’t look away even if I wanted to. Her hazel eyes have me under some kind of spell at this point. Next thing I know, I’m taking fast and hard thrusts into my now not-so-tight asshole. The full length of her shaft sliding in and out of me. I have no words to describe what I was feeling other than it was otherworldly. I was literally being fucked senseless.
“You enjoying this, you slut?” she said with a tone of authority.
Through moans and gasps, I respond “Yes, goddess. Please don’t stop. Fuck me harder.”
“Careful what you ask for.”
It was at this point I knew, I was in for it.
She slides out of me, and motions me to turn over. I do as she asks without second thought. I feel her slap her firm cock on each of my ass cheeks before she teases my entrance with the freshly lubed tip. She enters me again. But this time at a very slow, gradual pace. It’s agonizing. My body, my mind, my soul is craving her to fuck me again like she had just been doing. I let out a moan that almost became more like a groan.
“Oh? Is that not fast enough for you? Not quite hard enough? Oh that’s right. You wanted me to fuck you harder, like a good little whore. I guess I should oblige.”
Holy fuck.
With a swift slap on my ass that for sure turned it red in an instant, she took a hold of my hips and pulled me back so that her shaft was buried in side me. She then proceeds to slide in and out of me with the same force as she did when I was on my back. Except now, she could pull my hips into hers and seemingly increase the intensity of each thrust. I could hardly contain myself. My brain was in overdrive. The sensations were flying in faster than I could process. Her pace picks up, steadily increasing until I’m truly at the point of being railed. I truly lost track of time at this point. Reality no longer had true meaning, and I was riding a swelling wave of bliss.
I feel my core starting to tense, a very familiar feeling. I was getting close to climax.
“Goddess, I think I’m close to cumming,” I manage to get these words out as I’m trying to catch up to my breath.
Without saying a word, I feel her reach around me and start stroking me. All the while continuing to bury her ladycock as deep as it will go into me. I’ve given up on trying to process all of the sensations rationally, and I’ve given in to them. Goddess continues to tease my dick as she reaches into what I can only imagine was my stomach at that point.
Inches away from my ear, I hear that sultry voice again send shockwaves through my body, “Cum for me. Give your goddess that cum as a tribute for what she’s given you. Do it, my little whore.”
She strokes faster, her hands now demanding the tribute from my cock that her lips requested. My body could no longer contain itself. Between her stroking my dick, and the incredible feeling of her own cock deep inside me, I was beyond the point of no return.
My entire body shuddered, and I came harder than I’ve ever came in my life. I felt her hand slide off my shaft and down below to catch my cum as it drained from me. She lifter her hand, and chuckled.
“Very good. You’ve done well, my whore.”
A few more slow strokes, then she pulls completely out of me. I collapse on to the bed, breathing heavily as I try to catch my breath from this experience. My brain finally taking the chance to process everything that had just happened. Was it real? Was all of this a dream?
We each take the next hour and walk back through everything, give each other feedback, and then get ourselves and the room cleaned up. We grab some dinner, talk about the next time we’ll both be available to have another session, catch up on each other’s lives a little bit, then part ways. I give her a hug as she heads back up to her apartment, then I drive home.
Once I’m home, I almost immediately fall into bed and pass out for a nap. My dreams are almost a frame for frame recap of what had just happened.
I think I might have a bit of an addiction now.
If you made it to this point, thank you for reading my kind of long-winded story. Pardon any grammatical errors along the way. It’s 2am as I’m finishing writing this. Hopefully I’ll have more stories in the future to tell to a bunch of kinky strangers on the internet.
But for now, happy pegging!
Source: reddit.com/r/gonewildstories/comments/vmv1l6/i_took_my_first_rough_pegging_this_weekend_fm