I'll never forget that wonderful afternoon. From there Lily and I never really stopped. She adored having a good boy who would please her on command and I loved being used as such. When I asked Lily what made her decide to make a move on me, she said "I felt how much you were checking me out. Plus, I looked like someone who needed to be dommed."
I distinctly remember the week she got me a chastity cage. Lily would strut by naked the entire time and refuse to unlock me. God, I've never felt so much pleasurable pain like that. I had the biggest squirt, all over her face by the way, when she finally unlocked and jerked me off.
Everything changed the day, it arrived. I'd just gotten home from work and was about to shower. In front of my room was an opened package with a note. It read: put these on and meet me in my room. Inside was a pair of fishnets, a skirt, and a small bra.
This was new territory for me, but I never hesitated when mommy asked me do something. I got into my new uniform, just as she wanted. As soon as I put the skirt on, I could feel my erection grow. I didn't have time to think about this... mommy was waiting.
I opened her door and found darkness. I stumbled my way to the bed. I felt around and couldn't find her. "Mommy?" I called out. The door shut behind me. The lights came on and I was shocked at the sight.
Lily stood before me in the sexiest black lingerie I've ever seen on a woman. She also wore thigh high stiletto boots and spiked choker. I adjusted my own collar as I saw her. With her whip in hand, she stepped towards me.
"How do you feel?" She circled around me and lifted my skirt.
"Sexy... just like mommy asked."
"You're such a good girl."
"Girl?" I paused.
"Mmhmmm. I can't wait to break in your ass tonight." She cupped my ass cheeks. "Are you ready?"
"I guess so mommy..."
Lily spun me around and pushed me onto the bed. My cock made a tent in my skirt. I glanced down at my outfit; bra, skirt, and fishnets. In any other scenario, I would have been so embarrassed. But seeing how excited Lily was, I felt sexy in these foreign clothes.
The woman got on her knees. Her hands stretched across my legs. Her nails gently pulling on my tights. Without hesitation, she wrapped her fingers around my manhood. I softly moaned. In quick succession, she pumped me twice. I gasped as she did.
Our eyes met as she licked her lips. Her eyes widened as if she were going to take a bite. Her black lipstick sparkled in the dim light. I took a deep breath as I knew what was coming.
The sexy brunette leaned forward, pressing her tits on my legs, and wrapped her lips around my cock head. I felt her tongue dance over my sensitive area as she sucked me in. "Fffffuck... mommmy." I cried out. Her suction was almost too much... I could have squirted down her throat right there.
With a pop sound, her lips left my body. Her fingers take it's place.
"Honey?" She started to pump me again. I nod with acknowledgement.
"You've been such a good boy for me these past few months." I shiver as her sultry voice rings in my ears.
"I need you trust me, okay?" I nod back.