tagBDSMMy Weekend in Portland Ch. 02

My Weekend in Portland Ch. 02


"Forget that order," I said, as Ruth reached hesitantly for my fly, I have another idea."

"Yes, master," she said, and I shook my head impatiently.

"Don't call me master. That makes me feel like I'm in some stupid sitcom." Then I recalled the eagerly submissive way she acted toward her boss, invariably addressed as "Mr. Tucker."

"Call me Mr. K-----," I said, substituting my last name for Tucker's, and she nodded.

"Yes, Mr. K-----," she said.

Taking Ruth by the hand, I sat her down in a wing chair by the fireplace and settled into a facing chair. Then, for more than an hour, I grilled her quietly but insistently about every detail of her sex life. She was intensely embarrassed through much of my interrogation, alternately blushing and turning pale as I extracted her most intimate secrets. Once or twice I had to remind her she was my slave, so she was not entitled to withhold any secrets. Ruth tried to sit still, but sometimes squirmed in her chair, and her nipples were often erect.

I learned her breasts and pubic hair began to appear when she was 10, and she started menstruating soon afterwards -- much to her baffled horror. Her family was one of those that didn't discuss sex. By 14, she was wearing C-cup bras and fending off groping hands from classmates, teachers and even her parent's friends. Ruth lost her virginity at summer camp when she was 15, to a counselor who dumped her while his load was still dripping down her legs.

Unfortunately, she got pregnant from that brief encounter and her furious parents insisted on an abortion. They also severely restricted her contact with boys through high school. Away from home for college she had several brief relationships before connecting with a guy almost as repressed as she was. For two years their sex life consisted of him mauling her breasts and pussy through her clothes, while she jacked him off through his clothes. She was convinced they would get married after graduation, but he dumped her instead.

Over the ensuing years, a series of relationships ended when the guys involved found they couldn't get past first base -- ever. One of those relationships ended in a date rape she had been too horrified to report to police. Horrified because she hated being forced, and enjoyed it at the same time.

Ruth began to cry silently while telling me about the date rape. Most of her tears rolled down her cheeks, but an occasional droplet fell onto her full breasts. I loved the way her teardrops followed the curve of her tits.

"I WANTED to make love with him!" she said of the rapist. "I really cared about him. I tried to go a little farther each time we had a date. He played with my breasts a lot. But whenever he tried to get inside my pants, I just froze. I panicked and made him stop.

"At first he was understanding, but I could never explain why I couldn't go any further," Ruth said quietly. "He stopped calling and I got desperate. I called and told him I wanted to go all the way. He came over and we started making out on the couch. He opened my blouse and my bra, and that was okay. It was wonderful when he played with my nipples. He took off my pants, and that was fine. But when he tried to take off my panties, I panicked again and stopped him.

"He just looked at me for a minute, then grabbed me by the hair and dragged me to the bedroom. I tried to fight but he was too strong. He threw me on the bed, ripped off my panties, and forced himself inside me. I was so wet, it didn't even hurt. He came in a couple of minutes."

"What then?" I prompted.

"I was furious and I was humiliated," Ruth said. "I thought about calling the police. But I kept remembering how good it felt when he first pushed inside me, and the next time, and every time. After a couple of weeks had passed, it made no sense to call the police.

"I waited and waited for him to call again," she said, "but he never did."

Ruth's mysterious transfer from New York City to Portland resulted when her boss there became sexually obsessed with her. When he degenerated to the point of groping her in meetings, she sued and won a considerable cash settlement along with a promotion and transfer to the West Coast. Her obsessed former boss had been "exiled" to a sales district in Florida where he spent most of his days golfing with clients.

"Have you ever sucked your own nipples?" I asked, noticing that she clearly could.


"Why not?"

"I couldn't. That would be too nasty," Ruth said, blushing deeply.

"Have you ever sucked a man's penis?"

"No. Except ... "

"Except what?"

"The man who raped me made me suck his penis when he was finished."

"Did you enjoy that?"

"Yes ... no. I mean no."

"Do you ever masturbate?"

"Yes, sometimes."

"How often?"

"Once or twice a week. Whenever I can't stand it."

"Can't stand what?"

"Can't stand not touching my pussy."

"Do you come when you're masturbating?"

A pause, "No. Once."

"Can't you make yourself come more often?"

"I can't. It's too ..."

"You just stop when you get close to coming?"


"What do you do then?"

"I dress and go out somewhere public, or do aerobics, or sometimes I drink a couple of shots of tequila. I force my mind onto something else."

"Do you like tequila?"

"No, it makes me sick to my stomach."

"Has any man ever made you come?"

"No ... I don't think so. I think I was close a couple of times."

"Was one of those times the time you were raped?"


On and on I went, my dick straining in pants, wanting to drive deep into the pussy three feet from me, her large mound demurely covered by lacy white panties. Then things REALLY started to get fun.

"Have you ever had sex with another woman?"

There was a long silence. Finally I asked, "Why don't you answer?"

"It's been such a long time," Ruth sighed. "I put it out of my mind."

"What happened?"

"It was freshman year in college. My roommate came home drunk, late one night. It was hot. I was sleeping in panties, no covers. She just took off her blouse and fell on top of me and started kissing me. I remember how rough her bra felt against my skin. I didn't know what to do, so I just laid there, pretending it wasn't happening.

"She sucked my nipples for a long time, like she was hungry. I got ... turned on. I felt like I was going to explode. She sucked me and bit me. Then she just pulled my panties off, pushed my legs apart and started eating me. I didn't even know what it was called, just that it felt like heaven. I felt I was on fire. I came and came and came. I think she did, too. She was moaning and crying out while she was licking me. She had her jeans open and one hand inside her panties. Afterwards she fell on her bed and passed out. We never said a word about it, and she flunked out at Christmas. I heard later she went home and got married."

"You still think about her?"

"Yes. Sometimes."

"What do you think about?"

"Just ... you know ... doing things to her ... that she did to me."

"Is that the only time someone else has made you cum?"


"Stand up."

Ruth stood up hesitantly, and I beckoned her to stand close in front of me. I told her to take off her delicate white panties, and she slid them down her legs.

"Spread your legs."

Staring up into her eyes, I gently explored her crotch with my right hand. Her dark pubic hair was dense and coarse over her mons, thinning a little around her labia. A thin line of tiny dark hairs descended from her navel until they merged with her tangled pubes. Her hands hung by her sides, fists clenching and unclenching as my fingers probed her opening. Her outer lips were already engorged, fat, gaping open. Her inner lips were soft and slippery wet.

My fingertips traveled gently up and down her slit, discovering her beauty, while my eyes held hers -- dark and fearful -- exploring another kind of beauty. I found her opening, followed the rim all the way around, then slowly pushed a finger inside her, encased in warmth and wetness. Her mouth fell open and she was panting now, her hands restlessly wandering.

"Put your hands on your breasts," I ordered. "Play with them." Then later, "Play with your nipples," and she did, sighing deeply, her areolae puckering.

I pulled my finger out of her and suddenly the smell of her pussy was sharp in the room, delicious. I still held her eyes with mine, except when hers drifted shut under a wave of pleasure.

"Ruth," I said, and her eyes opened. "I'm going to make you come with my long, fat dick pushing in your pussy," I said, speaking clearly so she could understand every word. "I'm going to make you come with my tongue on your clit and my finger up your big, sweet ass. I'm going to make you come in ways I haven't even thought of yet, and now I'm going to make you come with my finger."

Staring down into my eyes, Ruth's mouth twisted and she gave a long, quavering moan -- I hadn't even really touched her. Then I was sliding my slick, wet finger up her slit to rub lightly over her hooded clit. Then I slid my finger down, rubbing her clit the other way and repeating the motion. Now she was gasping for air, her unfocused eyes staring wildly, straight ahead.

Pulling my finger up her slit, over her clit, then pushing down, sliding over her little button on the way down. A little faster and I looked up to see her tugging cruelly at her thick nipples, her head back and her mouth open. I speeded my finger and suddenly she was coming, coming hard, crying out uncontrollably and dropping quickly to her knees, her knees spread wide and her weight back on her heels, her hips thrusting. I leaned over, put my free hand behind her neck, and kept my finger sliding up and down her slit.

"Ah! Ah! Ah! AH! AH! AH! Ahhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!" came from her open mouth, then, "Oh fuck, oh fuck, oh fuck, FUCK, FUCK me!" like a fervent prayer for release, and she knelt in front of me jerking, groaning, dripping, spasming and altogether beautiful. I continued gently fingering her wet gash. Strength gone, Ruth finally collapsed backwards onto the floor and I followed her down, one arm around her bare shoulders, my hand still cupping her hairy soaking pussy, my middle finger inside her warmth.

She was whispering something inaudible, and I leaned over to put my ear next to her mouth.

"Ohgod, ohgod, ohgod," was all she said, over and over.

(End of Chapter 2 of 15)

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