When we first started dating, my girlfriend was painfully shy. We talked for months, we had many long, late night conversations before she felt safe enough to send even a single picture of her in her underwear. To me, she was the most beautiful girl I’d ever seen.
I still couldn’t wrap my head around why someone like her would choose a guy like me. She’d confess that I was the only boy she’d ever been with, and how terrified she was that I wouldn’t like her body. Her insecurity mirrored some of my own fears, but I made it my mission to be patient, gentle, and reassuring. Every time I saw her, I told her and maybe obsessively - how beautiful she was.
Then came that summer night, at this point we were 20 and 21. We were curled up watching a movie, windows open, warm breeze drifting in. I’d been secretly hoping all evening that she might finally make a move. I desperately wanted to but was so nervous in the moment. Up until then we’d only kissed and exchanged a handful of lewd photos. You can imagine how hard my heart was hammering when I felt her hand slide slowly under the waistband of my shorts.
She rested her palm over my bulge and kissed me. I think she already knew how submissive I was, even if I personally hadn’t yet discovered the full depth of it.
“Pull your shorts down,” she said in a quiet, but firm voice.
I froze. She’d never seen me before. No one had. My nerves must have been written all over my face because she softened, patted her lap, and whispered, “Come here, baby.”
I climbed onto her, legs straddling her thighs. She covered my eyes with one warm hand, while her other hand slipped inside my shorts and eased my cock free. I was already leaking, embarrassingly hard, completely undone.
I melted against her chest, breathing shallow, when she spoke the words that rewrote everything inside me.
“You want Mommy to milk that little dick, baby?”
A wave of emotions hit at once. Do I actually have a small dick? Is it enough for her? I felt so humiliated but felt an overwhelming rush of excitement. I’d called her mommy once or twice before as a half joking tease, but hearing her say it then, low and deliberate while her fingers wrapped around.
She continued to whisper in my ear while masturbating me, I begged to feel her mouth or her pussy, her breath making me shiver as her hand moved in slow, deliberate strokes along my length. Every word felt like it was melting me further into her lap.
That’s when she gently squeezed my balls and said
“Be a good boy,” she commanded.
I obeyed and returned with a “yes mommy”.
She rewarded me by tightening her fingers and speeding up the short, slick pumps. My hips bucked helplessly and moans turned into desperate little whimpers that grew louder with every pass of her soft hand. I was right on the edge, teetering, every muscle coiled tight.
I begged to orgasm in her grasp when all of a sudden she stopped, slapped my dick and said
“That little thing doesn’t deserve to cum without begging”
she forced me to beg for what seemed like hours before she gracefully allowed me to orgasm over her hand. While my eyes were still covered she slid her fingers into my mouth.
Since that first night, everything escalated fast.
The next time we were together, I begged desperately to feel her pussy. She denied me completely.
I wanted her so badly it hurt, but being forced to kneel between her thighs and eat her out while I humped my fleshlight against the floor, it was agonizingly hot. That was all I deserved, she told me. She had total control now, and I loved every second of giving it to her.
Then one day she “forgot” to close the bedroom door. I walked in and caught her masturbating phone in hand, scrolling big dick pics on twitter. She didn’t stop. Instead she looked right at me and ordered me to strip naked and kneel beside her on the bed. I obeyed instantly. I stayed there, throbbing and untouched, while she brought herself to a orgasm staring at thick bbc instead of me.
After that, I fell hard down the rabbit hole. I started stroking to cuckold porn in secret, the humiliation twisting into something addictive. One night I was so worked up, so lost in it, that the words slipped out in a shaky whisper while she was humiliating me.
“Mommy needs big cock.”
The moment I said it out loud, I knew it was over for me. No going back.
A week later she locked me in chastity. My cock stayed caged, useless except when she decided otherwise. The only way I’d ever get close to her pussy again was by worshipping it with my mouth or by wearing a cock sleeve strapped over the cage so she could ride that instead.
That brings us to now. In part this a confession, I want to watch her get pounded by a real man but I am so scared at the same time. I know she deserves it. I wish she would just send me a video of her getting railed. She teases the idea sometimes but I never know when she's joking or if she's waiting for my approval.
I feel like such a loser, what boy has a girlfriend for this long and is pussy free? If I'm really lucky she'll suck my cock or milk me with my fleshlight while scrolling porn looking at big cocks. I'm straining in my cage writing this, I would do anything to feel her sweet pussy, I’m so jealous of her dildo.
FUCK MY WIFE!
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