Recap from part one: April and I met on a dating site in 2016. With mutual kink interests and the desire to explore a few fantasies, we initially started out dabbling in male chastity and orgasm denial before delving into some light humiliation and her first pegging experience. After spending the week locked in a cock cage, we had met at a bar and then visited a local sex shop to purchase a strap-on. ——

We departed the adult toy store and headed for my house about thirty minutes south of the city. The anticipation continued building – definitely for both of us. I hadn’t achieved an orgasm in five days and the cock cage I wore remained a constant, conscious reminder of restraint. Every time I began to get aroused (which was quite often), my dick strained to no avail in attaining a full erection while the base ring would pull up against my balls and cause the most delicious discomfort. April had never pegged a guy before, and I could tell she was anxious but also gradually embracing a quasi-Domme mindset. As we journeyed to my house, her attitude became even more cool and collected, attempting to conceal her thoughts behind a slight devilish grin.

April had never been to my house before so I gave her a quick tour, offered a drink, and chatted about the property for a bit so she could ease into the new environment before we started playing (keep in mind, this was still the first day we met in person). It didn’t take long for her to become comfortable with the setting and the engagement shifted towards playtime. We reentered my bedroom and opened the toy bag. Had we known the dildo needing charging before use, I would have plugged it in to the USB on the drive. No matter – I plugged it in to catch a quick charge while she took the spareparts joque harness from the package and started extending the straps.

She asked if I wanted to wear the butt-plug for a bit as we waited for the dildo to sufficiently charge. I was happy to oblige. Her eyes stayed intently on me as I began to disrobe. My underwear was the last to go and she laser-focused on my crotch as the boxer briefs slid down and my cock cage was finally revealed. I stood on full display in front of a fully clothed April as she observed my naked body. In one smooth movement she took a step towards me and decisively, yet tenderly, grabbed my balls and gave an authoritative squeeze. Never having seen one in person before, she knelt down to admire the chastity device up close, running her fingers over both the plastic cage and my pre-cum leaking from the slit in the tip.

Her smile became increasingly radiant as she stood and handed me the butt-plug. I took it and the lube bottle with me to the bathroom so I could ensure my butt was clean before inserting the plug. It had been a long while since I had been anally penetrated, and I carefully coated the plug and my anus with a film of lube. I took a breath and relaxed my muscles, slid the toy into my hole, then wiped off the excess lube. It wasn’t a giant plug, but I definitely felt it; once inserted I quickly warmed up to its presence and became very comfortable with the feeling.

I returned to the bedroom and April had already donned the harness. She had removed her jeans but kept her underwear on and was attempting to adjust the harness fit. I approached…nude, plugged, and still caged, then knelt at April’s waist to offer a hand. She looked down at me and smiled as I began to tighten the loose straps around her thighs and hips.

I stood back and admired the sight. April’s tan, caramel skin contrasted perfectly against her light blue panties and the black / purple harness. The 8” dildo jutted out in front of her pubic area, and she wrapped her hand around the faux cock like it had always been there. We waited about fifteen minutes after getting the harness fitted to disconnect the dildo from its charging port and attaching to the harness. We had to loosen and readjust the straps, but the placement was a seamless process. I suggested she try out the vibrator settings to see which she preferred while I got some towels to lay across the bed.

It was go-time. She asked if I was ready, and I eagerly nodded. I went back to the bathroom and removed the butt-plug (and quickly rinsed it off) then headed back into the bedroom. Nothing had to be said. I got on the bed in doggy-style, placing a towel-covered pillow underneath me to arch my ass up for easy access. I felt the dildo poke my leg as April positioned herself behind me and began to drip lube on my ass crack. Her fingers worked the lube around my asshole then she took hold of the dildo and began to press its head against my anus. I relaxed my breathing as she maintained pressure on the toy and, all of a sudden, it popped in.

At first it was just a mass of pressure as she held steady with just the head inserted, but soon I could feel every curvature of the dildo tip. She asked if I was okay, and I breathlessly said yes. Her hands fell to my hips, and she began to apply more pressure, sliding the shaft further into my ass. After a few long strokes she dribbled more lube onto the toy and turned on the vibrating function. I can’t fully explain the feeling but, goddamn! Between my cock being constrained by the cage and the dildo pulsating away in my ass, all being underscored by April’s enthusiasm and willingness to explore, I was in a subspace not of this world.

She gradually increased the pace and began thrusting more forcefully. I can only imagine she was amidst the throes of orgasm or at least teetering on the brink, when she moved both hands to my shoulders, leaned forward, and thrusted HARD – I’m talking full-tilt. She bottomed out in my ass and delivered ten or so successive strokes then pushed my head down into the bed and pressed her weight on top of me. One of her hands found its way around my throat as the other hand pulled my hair, arching my chin to the sky as April continued pounding away.

The experience felt like it lasted a lifetime but couldn’t have realistically been more than twenty minutes at most. Eventually her thighs began to shake from muscular exhaustion and she fell motionless on top of my back, embracing me tightly in the conclusion of our kinky, sweaty escapade. We eventually got up, disconnected, and lay back on the bed fully spent. Well, her anyway. My dick was still pressing against the cock cage, straining for release, as we both observed the previously small string of pre-cum had now evolved into a continually flowing leaky mess at the cage tip.

April looked over at me, delighted and exhausted, and we briefly talked about how it felt for each of us. I wasn’t expecting it during that moment, but she said something that absolutely floored me: “Tell me more about this cuckolding thing you want to try…”

Part Three is on the way:)