Craig's DatebyMr James©
It was my twenty-second birthday and I was upstairs in my room, waiting, when I heard the front door slam shut and my Dad's voice calling from the lounge. I took a moment to glance in the mirror, and tighten the sash of my silk robe, so that my budding breasts pushed against the cool material. My nipples were hard against the cloth and I could see them in the mirror, making little tents in the white silk.
Dad had slipped off his suit coat and loosened his tie. I stepped closer to where he was standing and slipped my arms around his waist, resting my head against his chest and smelling the manliness of him. I turned my face up, lips parted and felt his mouth on mine. He thrust his tongue into my mouth and I groaned, pressing myself against him, feeling the swelling in his pants.
Dad pulled away, leaving me gasping, my heart racing in my chest. My little cock was hard and aching to be stroked, but Dad stepped back, pushing me away from him.
"Go upstairs, Teresa, your Mom has laid out some clothes for you. Craig has asked you to dinner tonight and I've told him you will be glad to go with him."
I could not speak, I had felt the heat of Dad's cock pressed against me and I had remembered the touch of his hands on the tight nubs of my nipples as he had pressed his hard cock into my tender asshole. I could feel the heat of my need for him building and I almost turned back to beg him to fuck me. Something in his tone of voice stopped me and I turned away to climb the stairs to my room.
Mom had been busy, laying clothes out for me . There was a new black shift dress, in heavy silk, black hold-up stockings and a lightly boned corset, with half cups to cradle my swelling boobs. Mom unfastened my robe and ran her fingers over the tops of my thighs and cupped my cock and balls, making sure they were still smooth and silky-soft. Then she reached back and took the corset, wrapping it around me and fastening it with the hooks and eyes down the front. She turned me around and tightened the laces, squeezing my waist and forcing my breasts higher. Mom watched as I rolled the sheer nylon of the stockings up my legs, settling the stocking tops comfortably at the top of my thighs. Then I slipped into the dress and looked around for a pair of panties. Mom read my puzzled look and moved closer, to whisper into my ear.
"Craig doesn't want you to wear panties." She murmured.
I slipped into the heels Mom had chosen for me and then sat still and patiently as she carefully painted my face. It took only minutes but, in that time, Mom had managed to hint at a more sluttish side to a young lady. Mom wrapped a fur stole around my shoulders and gave me a little push to wards the door. The heels leant a sway to my walk and I could feel dad's eyes on me as I slowly walked down the stairs. I knew that, from where he was standing, he could see right up, underneath my dress, and would realise that I had not put on even the flimsiest of panties.
Craig tapped the horn of his car impatiently and I only had time to snatch a kiss from Mom, who gently squeezed my cock through the thin dress. Dad rested his hand on the cheek of my ass as he pushed me out of the door. Craig had the car door open and helped me into the soft leather of the passenger seat. He spun the wheel and shot out of the driveway.
Craig drove fast, weaving through the slower traffic. Whenever he reached down to the gearshift, his hand would slide across to rest on my thigh for a moment, as he squeezed me gently through the silk of my dress. I kept very still and quiet, frightened that he would crash the car if I distracted him. It seemed a long drive and I wondered where he would take me. I knew that he had more than dinner on his mind, the hot caress of his hand, becoming more frequent now told me that he had no intention of a quiet meal and then dropping me at home.
Craig pulled the car off the road, onto the driveway of a large, imposing hotel. A valet appeared, as if from nowhere and Craig dropped the keys into the young man's palm. Then he led me up the steps, past the reception desk and into the elevator. The doors had barely closed before he stepped close to me and began to kiss me, his lips hard and demanding, while he kneaded the cheeks of my ass. He thrust his tongue into my mouth, forcing my lips apart as his hands tightened on my bottom.
The elevator doors hissed open and Craig took my hand, leading me along the corridor to a corner suite. He ushered me inside and closed the door behind him, turning the key and locking it with a loud click.
"Go into the bedroom, take off your dress and wait for me. "Craig commanded.
Meekly I obeyed, remembering the tone in Dad's voice as he had told me about his agreement with Craig. I unfastened the black silk and hung it carefully in the wardrobe and then sat on the edge of the bed. Craig stood in the doorway, unbuttoning his shirt. I could feel his eyes on me, running up and down my body. Stepping closer, he reached out and pulled the cups of my corset down, exposing the swell of my breasts. I could feel his fingers and thumbs closing over the hard points and then a sharp stab of pain as he pinched them, pulling them and stretching them. The spark of delicious pain in my tender flesh made my tiny cock stir, stiffening it and making it stand more upright.
Craig stepped back and looked me up and down, his eyes lingering on my stiff little cock. My nipples were hard points of desire, almost bruised where he had pinched and pulled at the tender nubs. Craig looked down into my eyes and saw the need in them. Laughing, he reached out and pinched the hard point between his finger and thumb, rolling the nipple between them, as if making a particularly delicate adjustment. I could feel the tingle shooting straight to my cock and I whimpered in the back of my throat.
"Do you want me to fuck your tight little ass, Teresa?" Craig asked in a rasping whisper.
I just nodded, knowing that I could not trust my voice, in case it came out as a trembling squeak.
"You're going to have to earn your fuck." He continued, "Stroke your pathetic little cock."
I took hold of my cock between my finger and thumb and started to stroke it slowly, easing the little hood of skin back from the tip. Craig watched as my fingers slid up and down the hardness of my shaft. I closed my eyes and laid back on top of the bed, my little cock sticking straight up between my finger and thumb. Craig had unfastened his pants and had his cock in his own hand, slowly stroking the length as he watched me.
"Wank your little cock until you cum all over your thighs and mess on our stockings" Craig ordered me, his voice hoarse as he stroked his own cock.
I tightened my fingers around the shaft of my cock and stroked faster and faster. My eyes were closed as I abandoned myself to the pleasure of a hand on my cock, even if it was my own. I could feel the bubbling of my cum as my balls tightened. I groaned as cum began to spurt from my cock, splashing onto the tops of my thighs and running over my fingers, covering me in my own slimy mess.
Craig steppes closer and stroked his fingers through the wet trails of my fresh cum that had splashed over my thighs. Carefully he smeared it over his fingers and then moved his hand lower, parting the cheeks of my ass and pushing a finger slowly into the tight, dark hole. I whimpered softly as Craig's finger penetrated my bottom, encouraging him to probe deeper. He slid his finger out of my bottom, leaving my asshole gaping.
Holding my knees and spreading my thighs wider, Craig knelt on the bed, his cock rubbing against my cock and balls. He took my hand, still slippery from my own cum and guided it to his hard cock, smearing it with the cum that was drying stickily on my fingers. I knew that he wanted me to guide his cock into my asshole, so that he could fuck me. I curled my hand around the head of his cock and pressed it between the cheeks of my ass. Craig lowered his mouth to my breast and sucked hard on the point of my nipple, biting it until the sparks of pain shot through my body. I could feel the head of his cock against the opening of my ass, stretching me as he pressed forward.
Craig pressed harder, stretching my ass with the swollen head of his cock. I could feel myself opening as he forced the swollen head inside me. Craig pushed my thighs further back and draped my knees over his shoulders, lifting my ass from the bed. I whimpered in a mixture of pain and pleasure as Craig thrust hard, forcing the head of his thick cock deep into my ass. His tight sac was pressed against my bottom as he pinned me to the bed, holding me down as I helplessly took his cock into my ass.
My whole ass felt as though it was on fire as Craig forced his way deeper and deeper. I could barely breathe and grunted as he drew back, then rammed into me again and again. The burning slowly subsided as he began to work the length of his shaft in and out of my bottom, his balls smacking against the tight cheeks of my ass. I could only grunt and push back against him as he pounded his thick cock into my anus.
Suddenly he thrust as deeply as he could and, as I gasped with the pain and the feeling of fullness, he leaned over to kiss my open mouth, thrusting his tongue between my lips and deep into my mouth. My body shuddered and trembled as an orgasm ripped through me, forcing the last droplets of cum from my cock to smear between Craig's belly and the black silk of my corset.
The tightening of my ass around his cock and the long groan I whimpered into Craig's mouth made his cock stiffen inside me. He jerked his hips forward, pushing so deep into my ass that it hurt. I could feel his cock inside me as he pumped thick ropes of his hot cum into my ass. Craig smiled at the expression of pain and joy on my face as he pumped his cock into my ass with long, plunging thrusts. I could feel the stinging splash of every spurt, as he filled me to overflowing.
As his cock began to soften and slip out of my ass, Craig kissed the tears of pain and joy from my cheeks and Grinned as he looked at the streaks of mascara and the smears where my lip-gloss had been smudged. There was a quiet 'plop' and a sudden gush of sticky cum as the head of his cock slipped out of my aching asshole.
"Your daddy was right," Craig whispered, "You are such a sweet fuck, as well as a delightfully slutty cocksucker."