To say I was bewildered would be a major understatement. The first night after the mountain bike ride and the resulting humiliation, I took the dildo out and stared at it blankly. There was no way I was going to voluntarily put that inside me, but I felt a huge sense of guilt at letting down both my stepmum, Sonia, and her friend, Lou, and an unexpected breathlessness of excitement.
The previous afternoon after we had made it home from the bike ride, Sonia had just handed it to me with a grin and said, "Practice every night."
I had no idea what she meant, and even less idea what I was practising for.
The following morning I tried to creep out the door to uni, but bumped into Sonia on her way back from her morning run.
Right in the doorway, she gave me a sweaty, breathless open mouth kiss and rubbed my rapidly expanding dick through my jeans. Once I was hard as rock, she whispered in my ear, "Did you practice for Lou?"
Mortified at having to acknowledge what I had or hadn't done to my arse, and at letting them both down, I just shook my head in silent response.
With her mouth pressed against my lips, she then murmured, "Well I guess we'll have to remedy that when you get back this afternoon. Make sure you're ready."
She then gave my arse a gentle squeeze, kissed me again, and pushed me out the door.
I may as well not have bothered going to lecturers. My mind was totally taken up with what could lie in store for me when I got home. I was so nervous I spent the day planning and strategising and eventually decided to visit a pharmacy for a syringe and some lube.
I have never been so mortified than having to front up at the counter to the attractive sales associate with what could only be products to prepare for anal.
I then spent a good half hour locked in a disabled toilet rinsing out my ass, pushing out water until it ran clear. I then applied a small amount of lube and headed off home.
As I walked up the drive, the lube made my ass feel weird, wet and slippery, but reminded me what could be in store for me, turning me on and terrifying me. However, when I snuck through the front door, I was confronted by Sonia sitting on the couch drinking wine with another woman sitting beside her chatting animatedly.
As a feeling of relief and disappointment flooded me, I noticed the dildo stuck to the end of the kitchen counter, hanging lewdly right in front of them. Beneath the dildo were some carefully folded towels to make kneeling on the kitchen tiles easier and no doubt catch any stray fluids.
My heart sank to the pit of my stomach as I realised I was the floor show for these two maniacs.
Embracing every ounce of dignity I still owned, I decided to walk right past them and pretend not to notice the phallic object.
Apparently reading my mind, Sonia rose from the couch and wrapped her arms around me, kissing me passionately while grinding her hips against my rapidly growing erection. She then pulled her head back, and with her lips a millimetre from mine whispered, "Time to show us just what a naughty boy you are. You never know, one of us may just let you fuck us." The, "Fuck," was deliberately drawn out and emphasised, jolting me to the core.
Without further encouragement, she deftly pulled off my t-shirt and began caressing my chest as she kissed me violently. I was so focused on meeting her oral assault, I barely felt her unbuttoning my jeans and tug them down with my boxers until I felt the cooler air on my ass.
As she continued to suck my tongue and violently probe my mouth, I was surprised to feel her hand slip between my ass cheeks. With a combination of horror and longing I felt her slide a finger into my clean, lubed arse.
With a sigh of surprise she immediately pulled away from me and proudly stated, "What a good boy. You did come prepared for us."
For the first time I became conscious of the other woman again, and very aware of my embarrassing state. There I was, basically naked, with my rock hard dick sticking out, and my jeans and underpants around my knees.
With a surprisingly perfunctory voice, Sonia then asked the new comer, "Do you want to undress him and help him fuck the dick, or shall we just watch?"
With her gaze switching from my stiff cock to my mortified face, she replied, "Oh, let's just watch. For now."
Smiling, Sonia turned and started a video going on a laptop I hadn't noticed before. It was sitting on the floor, right in front of where I would have to kneel, and was now playing what was clearly 50 minutes of anal compilation. Sauntering back to the couch and grabbing her wine, she quietly said, "Time to show us what you can do."
My poor dick was now turtling, like it was trying to disappear into my body. However, feeling awkward, humiliated and distressingly excited, I kicked off my shoes and pulled my jeans off one foot at a time.
Staring at the obscene dick, the video, and the two women, I moved over to the kitchen counter and knelt with my arse to it. I glanced at the two women sipping their wine once more, then decided it would be easier to stare at the floor.
With my head down in embarrassment, I then backed up to the dildo and positioned it against my anus, ready for total humiliation and a bit of pain.
My plan to try and forgot about the women was immediately thwarted, as Sonia then commanded, "Look at us while you fuck that big dick."
I lifted my head and pushed back, feeling the dick enter my arsehole surprisingly easily until it hit my sphincter. Glancing at a woman getting pounded by a strapon double the size of the one I was working, I pushed harder, only for it to feel like I was being ripped in two which catapulted me forwards.
Sonia's voice re-entered my world, "Keep going, fuck it like those girls do."
With a shaky breath I started again, feeling it part me, enter, and hit the muscular block. This time I felt it go slightly deeper until I couldn't take it. With slightly more control, I moved forward and started again, Sonia's encouragement ringing in my ears.
The fourth or fifth time, it slid past my sphincter, surprisingly deep into my ass. Again I pulled forward, and -as instructed by Sonia - I rode it back and forth, each time going deeper until I could feel it's balls hit my ass.
By this time my erection had returned, and a small pool of precum was beginning to form on the ground between my legs. With Sonia's command, I began to ride it faster while the pressure built in my aching penis.
Grinning, Sonia slipped off the couch and stood in front of me, fortunately stopping my solo dildo pumping.
Lifting my chin up, she then softly said, "Slide it right in."
I did as she said, while she pulled her summer dress over her head and quickly slid down her knickers, leaving her beautiful body naked except for her bra.
With the dildo just about rupturing my colon, I then began to lick and suck her wet clit. As normal, Sonia's hands were on my head, guiding me and forcing my mouth hard against her.
I heard her cum really fast, her breathing turning ragged and a the occasional, "Fuck," escaping from her.
She pushed my head back when she was finished, and proudly muttered, "Fuck, you are starting to get good at that."