Again.
And I was wearing Justine’s old PE kits – including her bra and navy blue knickers.
Again.
“I have to admit, seeing the lump of your raging hard-on does something for me,” Justine said, touching up the last of the make-up she had applied to my face. My lips were now a dramatic scarlet and Justine had gone to great pains to highlight my cheekbones and eyes.
“Not as much as your raging hard-on does for me, Mistress.” Justine’s mouth twisted into a smile as she wanked the shaft of her strap-on.
“There,” she said, standing back to admire her handiwork. “Have you been thinking about being on your hands and knees on my bed, getting fucked like a girl?”
My stomach tightened as I nodded. From Justine’s expression, I was sure that my cock twitched, making my excitement visible.
“Me too. I’ve been thinking about it a lot.” Other commitments had kept us apart for a few weeks, but none of that mattered now. I was back in Justine’s bedroom, dressed in the gym clothes from her school days waiting for her to take my anal virginity. “I never imagined I’d take a boy’s virginity like this.” Justine’s voice had a distant, breathy quality and as I watched, her nipples pulled into tight, hard peaks.
Those nipples liked to be pinched, pulled and nibbled – especially when they’re coated with my spunk.
“Uhhhh...” Justine groaned as I gripped her left nipple, squeezed it with my thumb and distorted the curve of her breast by pulling. Touching her bare body made me aware of her clothes against my skin… and as Justine pressed against me, she became aware of my body under her clothes.
“I like it when your cock’s trapped in my little blue knickers.” I whimpered as she talked dirty to me. “Such a big fat cock,” she said, making my jaw clench as she slipped her hand under my gymslip and took a hold of my cock and balls through her underwear. “For such a petite little girl.” Searing heat filled my nerves as Justine wanked my cock. “How long since your last orgasm?”
Justine already knew the answer to this question. “Ten days.”
“Ten days of torment, no doubt.” Justine grazed the length of my cock with her fingernails. “The wait will be worth it, I promise.” Something flashed across her eyes, and I sensed that there was a plan “I’m going to make you eat all that lovely spunk.” Justine never was one for keeping things to herself. “But first,” she said, pulling away and circling me. “I want to fuck you.”
I gasped as Justine helped herself to a handful of my hair and pulled my head back. “Are you OK with this?” she whispered in my ear. “I’m afraid that I’ll hurt you. I really don’t know what I’m doing.”
“Bring it on.”
“You cocky bastard,” she said, throwing my head forward in disgust. I sprawled theatrically across her bed with my bum held high, deliberately showing my blue knickers and my white, knee-high pull-up socks. Justine almost smiled but managed to school her face back into a stern expression. “I’m going to enjoy sticking my cock right up you,” she said, waggling the cock in what she imagined being a menacing manner. “Deep inside your tight, virgin hole.”
Justine flicked my skirt up and pushed the tip of her cock into the centre of my blue-knicker-clad bottom. She accurately speared right against my arsehole, which caused a wave of panic to flood up my spine… and a flood a viscous cock-glue to leak into the blue knickers. That desperately-stretched cotton which had protected Justine’s pussy during Physical Ed was now the only thing protecting my anal innocence.
“Take ‘em off,” Justine snarled. “And you’d better be all nice and smooth underneath.” I was super-smooth: the fantasy of my feminisation was important to both of us.
My stomach did a flip of excitement as I exposed the root of my cock, my balls and my arsehole. Out of Justine’s sight, I wrapped her skirt around my cock and wanked it gently, enjoying the sensation of my juices leaking into the material.
“Such a tiny little thing,” Justine commented, jabbing a sharp fingernail against my anus.
“Oh fuck!” The fingernail felt like a bee sting and my hips shot forward involuntarily, driving my sensitive cock deep into the tunnel of Justine’s gym skirt.
“I don’t know if this is such a good idea.”
It’s a good idea. “I need you to be bossy and bitchy.”
“Bossy and bitchy. Right.” I prayed that Justine wouldn’t lose her nerve – she sounded as though she was right on the edge.
“Please do it.” I flinched as the fingernail returned and tried pushing in dry. There was no way it was going to work with no lubrication, although there were plenty of lubricating juices leaking out of my cock.
I whimpered as Justine spat on me; my excitement rising as she disrespected me, as she dominated me. Her sharpened nail brushed my anus once again but this time, it pushed in hard. Pinpricks of electricity shot along my nerves as she penetrated me.
“It’s so tight,” Justine murmured. I could feel her finger in my arse and my back arched as the slender digit parted my inner muscles. “Isn’t your prostate somewhere in here?” My cock jumped as a claw scratched across something sensitive inside. “Sorry.”
“Please.” I didn’t care that I was begging. There was a new kind of tightness gripping my balls as Justine finger-fucked my arse. She kept spitting into the slippery pit of my anus as she pumped her finger slowly in and out. My muscles loosened and then tightened, straining to push me over the edge. Suddenly the willingness of my hole to be fucked translated into movement of my hips.
I found myself thrusting back on Justine’s fingers.