The doorbell rang. Through the glass panes of my front door, I could see him shivering with a brown-bagged bottle of wine tucked underneath his arm. When I let him in, he thrust the bottle at me, leaned forward to give me a quick kiss which was a slightly painful bump of his cheekbone against mine. Hmmmm...he was very nervous.
He was a rather conservative type – blue dress shirt, brown hair cut short, carefully combed and parted on the side. Even his blue jeans looked formal, they were brand new and stiff as if they were ironed. Ironed jeans? Just how uptight is this man? It was apparent he had taken quite a bit of time to get ready for our first meeting. To keep him calm and make him feel more at ease, I kept my movements slow and deliberate. I turned him around, slipped his leather jacket off and hung it on the banister post. Told him to sit down while I open the bottle of wine.
He sat at the table, crossed his arms and looked around everywhere but at me. There was no expression on his face except for the tight lips.
"This man really needs a glass of wine," I thought, "he's far too nervous."
While opening the bottle, I thought about the obvious contrast between the two of us. I was wearing a silk skirt that reached just below my knees, a buttoned silk shirt that was tailored at the waist, pointy leather boots with three inch heels. All black. I kept my make-up simple, just red lipstick and black mascara which heightened the contrast of my dark brown hair and very pale skin. For a brief moment, I felt overdressed but then remembered, based on our conversations online, then he liked a woman to dress that way. Tight black clothes, red lipstick, suggestively domme-ish.
When the cork was released from the bottle, it gave a slight popping sound that made him look at me. Oh good, eye contact, finally. Brought the opened bottle and the wineglasses over to the table and sat down, crossed my legs and rested one elbow on the table. He quickly grabbed the bottle by the neck and poured for both of us, sloshing the wine only slightly. We held up our glasses and without a word, clinked. A bartender told me once, that in medieval England, glasses were intentionally clinked hard enough for the wine to spill over into each other. So that one could trust that the other hadn't poisoned the wine.
Did he trust me now?
On the table was a black and brown leather backgammon board with ebony and ivory pieces already placed in position, waiting for us to play. Right away, we began playing so that he could learn for he had never played this game before. And certainly had never learned to play it my way. This poor young man, he had no idea what he was in for.
He lost the first round, understandably. He was new and had much to learn still. I smiled and told him that each time he lost, he would have to do something for me. It was the rules.
He wrinkled his forehead a bit, wondering what I was talking about. I ordered him to unzip his jeans and pull out his cock through the opening of his boxers. He stared at me for a few seconds, trying to determine if I was being serious. He was not the type who would appreciate being humiliated. I returned his gaze steadily, raising one eyebrow expectantly. Having made up his mind that indeed I was not joking, he fumbled to unzip and pull out his cock. I was loving this, a fully dressed man sitting at my table with his cock looking so vulnerably exposed. I couldn't wait to play another game. Judging by the looks of him, neither could he.
We played another round. He was so self conscious and flustered that he lost again. When I gave him a little grin, his adam's apple rappelled up and down his throat. I could tell he was thinking, "what the hell did I get myself into?"
"Pull down your pants."
This time, he didn't hesitate. While his face was turning as red as the crimson lipstick I wore, he gingerly pulled his cock back through the zipper and within seconds, his jeans that he had carefully ironed were now bunched around his ankles. He looked at me to see if I approved. I deliberately took my time to take in the view of this man. From where I was sitting, he appeared fully dressed for he was sitting right up to the table. I didn't smile knowing that this would make him more nervous and unsettled.
He looked over to the wine bottle. Giving a slight nod, I permitted him to have another glass. With a slight jerk of my head, I made it plain that he should move back from the table enough so I could see more of him. He pushed back a little, obviously feeling shy yet it was obvious he was also excited.
Another round was played. This time I lost. On purpose, for I had a game plan unbeknownst to him.
His eyes widened at the realization that he had won, unsure of what to expect. I rested my foot, encased on a knee high boot on the edge of the chair between his knees and lightly rested it against his genitals. The black skirt I was wearing naturally slid down my raised thigh and he saw that the sheer black pantyhose I was wearing reached only to the top of my thighs. His mouth fell ajar a little. He tried very hard not to rudely gawk while casting furtive glances to see what I was wearing underneath that skirt. His hands moved forward to touch the leather boot but just before they did, I snapped my fingers and gave a warning shake of my head. His hands fell to his sides. But his cock was beginning to thicken and harden, the veins well on their way to being fully engorged.
