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.

“Do you like it when I touch your breasts?”, he asked.”

Yes”, I whispered.

“Then say so.”

“I like it when you touch my breasts”.

I hung my head; embarrassed and ashamed. He turned me around and removed my blouse.

“Continue your walk”.

Clad now only in very short and tight black boy shorts, I resumed walking, cognizant of the revealing nature of my panties through the way it hugged my vulva and behind. He suddenly called on to me to lift my legs higher as I walked. I did so, transforming my walk more into a sort of march. After another lap, he told me to remove my panties. Completely nude now, I continued marching with Jack instructing me to lift my legs yet higher and higher as I walked. I began to feel utterly exposed as he told me first to rock my shoulders back and forth and then to twist my torso as I walked whilst turning my head opposite to the direction of turning my body. I maintained this walk for a while, twisting my torso to the left; head to the right, then torso to the right; head to the left. As I continued ... feeling utterly ridiculous ... Jack told me to open my mouth as wide as possible and close it and repeat as I continued the march.

“Keep marching, but now swing your arms out in front of you and then back behind you as you march. Good. And now to the sides; swing back and forth. Keep opening your mouth; closing your mouth. Good girl.”

I was feeling more and more uncomfortable, though physically I welcomed the break from twisting my torso which had me starting to ache.

“Lift your legs higher as you. As high as possible. Higher. Yes, that’s it.”

My knees were now coming up to my breasts ... I felt like some sort of an obscene crab and the air in the apartment felt quite cold on my private areas.

Finally Jack stopped me with his condescending “Good girl”. While I could see an aroused bulge at his crotch, he was still fully clothed.

“Now get onto your knees.”

I crouched down on my knees and rested my head on my arm on the cold floor. Jack left for the kitchen and returned a few seconds later with a jar of Crisco and a surgical glove. Jack crouched behind me. He massaged my neck rubbing my skin, then progressed to my shoulders, my underarms, then my sides and flanks. His hands felt cold to the touch at first, but quickly warmed with the friction of his rubbing. He then opened the can of Crisco and smearing some on his hands, began to revisit the parts of my body he had been massaging, this time generously rubbing the fat into my flesh. He reached for the tie that held my hair and undid it, allowing my black hair to flow freely down my back and he pushed it to the side. He put the surgical glove on his right hand and then stroked my hair with his left, whispering for me to relax. He dipped his right hand into the fat and brought some up, smearing it over my behind and with a generous amount going into the cleft between my buttocks. His finger swirled around circling my anus and then he gently pushed his finger inside me. I shivered and began to crawl forward, but he gripped me tightly, pulling me back.

“Easy. Just relax your muscles. Just relax.”

My pulse was racing and my throat went dry. He pushed his finger deeper into my anus while keeping a tight grip with his left hand about my jaw, pulling me back to him so that he could easily penetrate my rectum with his finger. After using more fat, he forced a second finger into me and as my anus widened he began plunging the two fingers in and out in a rapid rhythm. I stopped resisting as my anus becam more accustomed to the intrusion.

Feeling my acquiescence, Jack reached underneath me with his left hand while continuing to plunge in and out of my rectum with his right hand. Pulling my pubic hair firmly in places, making me gasp in pain, I could feel his own excitement building; though still fully clothed, I could feel his penis hard through his trousers against the back of my left thigh. His fingers found my clitoris and began to massage it while continuing to thrust in and out of my rectum with the fingers of his other hand. I gave a stifled scream as I orgasmed and collapsed on the floor breathing heavily.

After a minute, Jack circled me and squatted slightly, pulling his pants and underwear down. His penis, stiff and erect sprang out. Sensing his desire, I swirled my tongue about the glans of his penis ... licking the shaft ... the scrotum ... coating the entire organ with my saliva. Then taking the penis fully in my mouth I began to suck slowly but fully with much saliva to keep him wet. He began slowly to piston his penis down my throat, grabbing my arms and stretching them both high wide as he fucked my mouth. Suddenly his penis began to spurt in my mouth, he held my head firmly still as he spurted, my throat swallowing frantically to keep up with his ejaculation. Despite his extreme sexual excitement as betrayed by the intensity of his orgasm, Jack maintained his outward calm throughout.

Jack pulled up his underwear and trousers and told me to dress. We rode down the elevator in silence. He drove me to my apartment; the only words exchanged had to do with getting to my place. Before leaving the car, Jack asked me if I would be interested in experiencing a much heightened form of the night for a full week; weekend through weekend. My mouth dry, I nodded.

“When can you arrange to take off the week?”

“The week after this one; I have some time coming to me.”

“Good. I will be in touch through Frank. Only pack the toiletries you will need. Everything else will be provided.”

Without a “Good night” from either of us, I left the car and went up to my apartment.