Trust Me

A sub agrees to try pegging for the first time.
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"Puppy! I'm home!" The unmistakable voice rang through the house.

I sprinted toward the front door and straight into my Mistress' open arms. She wrapped them tightly around me and I nuzzled her chest. Whatever else I'd been told, there were a few advantages to being short. I looked upwards; into her bright blue eyes, slightly magnified by her glasses.

"How was work, Mistress?" I asked, though I could tell she was excited about something; she was teeming with it.

"Same old, same old. But I brought home some more toys for us to play with." She brushed her shoulder-length blonde hair out of her eyes and picked up the bag she'd dropped on the floor. "Come on Puppy. Upstairs."

She practically bounded up the staircase, her fair ass swaying to and fro. I followed enthusiastically; as fun as it had been up to now, I was getting a little bored with her handcuffing and blindfolding me and riding me cowgirl with little change. It felt strange to think that, when 3 or 4 years ago I wouldn't let either the blindfold or handcuffs anywhere near me.

Mistress crashed through the bedroom door and jumped onto the bed. I followed suit, infected by her eagerness. She began taking things out of the bag at random. I picked them up and examined them in turn before replacing them next to her:

Black furry handcuffs, a short crop, lacy pink lingerie, a telescopic spreader bar, boob-shaped cola sweets (yes! my favourite!), wax strips-wait, wax strips? I raised an eyebrow at Mistress and she snickered "They had a buy two get one free offer, and I'm getting tired of cutting my legs shaving." Breathing a slight sigh of relief, I went back to the now finished-pile. Lemon-scented lube, another wax strip pack and...my face fell as I picked it up: a realistically-sculpted strap-on dildo.
My mind was racing. Mistress had talked about trying anal before. I'd always laughed it off as a joke. Now she'd bought this strap-on, I knew she was serious about it. I just stared at it, speechless. The temperature of the room seemed to drop several degrees as Mistress noticed my reaction to the dildo.
She reached over and took it from me; I looked at her face. The trembling of her lips betrayed her emotions, even if her tone of voice didn't. "Pu-" but she stopped herself. "Nathan, do you trust me?"

The use of my real name acted like a stimulant; my head slow down enough to think. I loved her, and I'd trust her with anything, but this... Was I really ready to do this? I'd seen videos online of pegging, and I could tell how enjoyable they were for the guy in them. But what if this wasn't something I liked? I wasn't worried by the idea of being assfucked nearly as much as at the prospect of disappointing the woman I loved most.

"Mistress-" I began, but she cut me off.

"No. We're equals tonight, Nathan." Her eyes looked directly into my own as she said it.

"Okay... Hayleigh, I'm just worried... I know you've looked forward to this, but... what if I don't like it? I... I'd hate myself if I let you down." I explained.

"I'd be even more let down if we never tried it." Hayleigh replied. "When I was in college, I tried dating a lesbian who had a crush on me, but I found that it wasn't for me. I look back on that and I'm glad I tried it, because otherwise I wouldn't know I wasn't into girls."

I was still uneasy. It clearly showed as I tried to think about what to say. How to convey my thoughts. Hayleigh spoke up again: "Nathan, if you still don't want to do this, I won't hold it against you. We agreed when we began this relationship that sex wasn't a priority. I just... I genuinely think you'd enjoy it. A chance is all I ask for you to give this."

A chance... I knew a thing or two about chances. Chances to stand up to bullies. Chances to pick up your grades because they dropped because you lost a family pet. Chances to... to find a loving mistress who cared for you and made sure any welts and bruises were covered in lipstick before you drifted into sleep when your last relationship could be described as "abusive" at best.

I made my choice; I wasn't the kind of person to let fear dictate my actions, and I wasn't going to start now. "Okay, I'll do it but..." I paused for a second. "No blindfolding, no tying me up or anything else. Just... just you, me and..." I couldn't bring myself to finish.

Hayleigh leaned over and gently kissed me on the cheek. "Thank you, Nathan. Now, just strip off and lie down like so many times before, but spread your legs apart. Let me do the rest." I obliged, my heart racing nearly as fast as my mind. Was...was I really about to do this?

Yes. For her.

I kept an eye on her stripping herself off as I did that same. She wasn't large or plump by any means, but she wasn't scrawny or thin either. In looks, she was commonplace-like any other woman. But her personality, her motherly and kind nature and her sheer untempered kinkiness made her one of the most beautiful women I'd known. I still felt lucky to have her.

She poured a measured cup of the lube onto the tip (filling the room with the scent of citrus fruit) and rubbed it down the shaft. It glistened slightly in the afternoon sunlight, looking a lot less menacing. Hayleigh bent over me, placing a hand on the covers to the right of me while guiding the strap-on to it's destination with her right hand.

My nerves overcame me for a moment. "Hayleigh..." I whimpered. She looked up at me, her hands ceasing their movements. I could feel myself shaking. "I'm sc-scared..."

She pressed her torso against me, put her lips to mine and whispered "Just remember to use your safeword if it's too much. You may not be my Puppy tonight, but you're still a good boy."

Hearing those two words in my ear... I suddenly felt like I could walk through Hell itself. I felt my resolve bolster and gave a jerked nod. She raised herself up and I felt the plastic brush against my opening. She moved the dildo up and down, teasing my hole, testing it. She began to push against my hole, and despite the internal screams of protest at the intrusion, I opened up.

I felt the strap-on break into my ass and winced slightly. I gripped the covers hard as Hayleigh slowly, inch by inch, pushed inside. I bit my lip to stop myself crying out as the dildo penetrated me. As my anal virginity faded into nothingness. But it was more uncomfortable than painful. I felt her hips press against my ass and knew the dildo was fully inside.

I looked up from the sight of her belly into her face. I gave a small nod that Hayleigh returned. She pulled herself back as slowly as she'd entered. It felt slighty relieving, feeling the void in my ass return. But as slowly, the void was refilled with the plastic invader. I could only thank whatever gods may be for the lube. Hayleigh repeated her slow and deep thrusting, but didn't go in all the way. Maybe something of my discomfort showed on my face.

This felt strangely nice. Hayleigh pushed inside deeply enough for the dildo to press against my prostate, (which she knew the location of through lots of experimental fingering), but not so deep that her hips pressed against my ass. At a guess, she was only pushing halfway inside. Hayleigh also kept her eyes locked on my face, looking for any signs of tenderness as she gently thrust.

"Deeper..." I whispered, reassuring her.

"You sure?" She asked. Her voice was halfway between surprise and concern.

"Positive." I nodded. "But you owe me another pack of cola boobs for this..."

Hayleigh laughed, leaned up straight and took the underside of my knees in her hands. I only now realized my legs were feeling numb; she began to thrust slightly harder, using them as handles. She drilled into my ass almost recklessly, but the dildo pressed against my soft spot with every push.

To my shock, I found myself quietly moaning every time she pushed into my opening. I couldn't deny it... I liked this. Judging from Hayleigh's smirk, she could hear my little squeals of pleasure. Indulging her, I began to moan louder for her, letting out an audible sigh everytime she filled my ass with the plastic dick.

Hayleigh let go of my left leg and began to stroke my cock in time with her thrusts instead. The familiar feeling of her hand wrapped around my shaft awakened me to another familiar feeling; one of building pressure. To say I was surprised would be an understatement: was I really going to come from being anally reamed?

"I'm... close..." I breathed.

Knowing how to push me over, Hayleigh's met her lips to mine and pushed inside me fully, jerking my cock with such speed her hand might have been a blur. A second later, I felt my restraint shatter and my cum shot over my torso in two large spurts, causing me to moan into the kiss. After a pause, Hayleigh slowly pulled out of me. She lay down at my side and I rolled over her, my face pressing in-between her modest breasts.

"Mistress?" I asked.

Her hand ran through my hair. "Hmm?"

"I love you." I muttered into her chest, turning my head to the side.

"I can tell." she smirked. I felt her lips kiss my forehead. "I love you too, Puppy."