Chapter 1

I first met Jack at Ellen’s wedding. Ellen was a coworker of mine. I was talking to Frank, another coworker, when Jack came up to us, greeting Frank. They spoke together for a while, mainly ignoring my presence. I saw Jack arch an eyebrow at one point; Frank smiled and then Jack went away. I felt somewhat uncomfortable during the exchange. I never felt very comfortable around Frank; he was about fifteen to twenty years older than I was (I was 26 at the time) very burly, hairy, and with a dark complexion. He was somewhat squat in stature; heavy with large rough looking hands. I knew he fancied me as I would notice him looking at me from time to time in what I felt was an inappropriate manner. I was oddly both repulsed and drawn to him. Jack, on the other hand, I found to be very handsome; he was tall and fair complexioned with a good build and a somewhat stern looking visage; perhaps about forty years in age. I had hoped for more interaction with him after he approached us, but he basically ignored me, focusing his attention on Frank. After a few more words with Frank, we separated to mingle with other guests at the wedding.

Towards the end of that week, Frank approached me and told me that Jack had been attracted to me and wanted to take me to dinner the following night. A little surprised, I consented and he said Jack would expect to meet me at a restaurant at 7:30 the next night. The restaurant was not far either from work or from where I lived, and was rather posh; I had never eaten there.

I dressed in a way to show off what I felt were my most attractive attributes. Describing myself, I am pale, a bit thin with longish black hair and blue eyes; leggy with full firm breasts. This evening, I wore a black skirt and white blouse, cut a bit low to reveal some cleavage and tied my hair back. Usually I do not wear a bra and my thin blouse allowed the outline of my nipples to show. I do not generally wear much make up save for mascara.

Jack met me at the restaurant on time and ushered me in to a reserved table. He pulled a chair back for me to sit, placing a hand on the small of my back to guide me in front of the chair and then pushed down gently, but firmly on my shoulders as if to seat me. Our conversation was light and general, but seemed to focus on me; he asked of my background; where I grew up, my education and other neutral topics. When I asked about him, he tended to answer shortly and steer the conversation back to me.

After dinner, we arose and he told me he had another activity planned for us for the night. He reached for my coat and put it around me and took me to his car. It was a large, dark, four door sedan. He opened the door for me, was sure I was entirely inside, and then closed the door. He entered from the other side. Jack turned towards me and said “Excuse me” as if he was about to look for something, but instead told me to lift my behind. Slightly bewildered, I lifted my bottom off the car seat and was taken aback when he pushed my skirt upwards above my hips.

“Pull your panties down to the middle of your thighs”, he said calmly.

I felt a fearful chill run through me, but after a slight hesitation, I did as he instructed.

“Good girl. Now sit back down on the seat.”

I sat back down, my bare buttocks sitting on the very cold vinyl of the seat.

“Spread your legs a bit.”

I complied. He placed his index finger at my lips and pushed. I opened my mouth and sucked his finger as he obviously expected. Then reaching down between my legs, he pushed his finger into my vagina, pushing it in, back out and repeating several times. I began an excited whimper but he told me firmly to be still. I fell silent, looking down into my lap. He stopped and then started the car.

He drove north for a couple of miles to just beyond the downtown section of the city and then west, entering a rather rich neighborhood. Parking in a garage, Jack told me to pull my panties back up. We left the garage and with his hand on my elbow, he took me to a swank apartment building and ushered me into an elevator. The elevator took us up swiftly to a high floor. We left, went down a hallway laid with expensive carpeting and into an apartment. Jack took my coat, and hanging it up, asked if I would like a drink. I declined, thanking him. I wanted him to touch me again.

The apartment was large and especially long; the living room and dining room were contiguous to form one long room with a kitchen adjoining the dining room. The three rooms were floored with large shining white tiles. Jack approached me and took my handbag from me setting it down on the nearby couch. I began to reach for him, but he gripped my shoulders firmly and slid his hands downward, pinning my arms to my sides.

“I will initiate all of the actions. Just do as I tell you to do. Do you understand”?

My pulse quickened and I nodded silently, perhaps a little fearfully.

“Good. Walk down the length of the room and back.”

I complied with his instruction. He gazed at me as I walked the long length of the living and dining rooms.

“Remove your your shoes ... now your stockings. Good. Continue to walk.”

I began my second lap, the room was quite cold and the tiles felt especially cold to my bare feet.

“A little faster, now.”

I complied, picking up the pace. At the far end of the room he called to me to remove my skirt. I did so, and continued my walk. The lower part of the blouse covered my panties, my bare white legs looked soft and vulnerable.

“Good girl”, he said.

Jack unbuttoned my blouse, revealing my breasts. He reached into the shirt and began to massage me ... rubbing my breasts ... then kneading them as if he were working with dough.