Kindness of Strangers

He spread my thighs further apart and bending down, positioned himself between my legs. I had only had sex with my boyfriend a few times, but he was a boy, and his dick was a boy's dick, small and thin, Mr. Wolowitz had a man's cock, long, thick and hard. He entered me slowly, obviously enjoying the warmth and tightness of my pussy with each thrust. "You're so wet and tight, little girl, just like I knew you'd be," he said. Moaning loudly as my pussy contracted around his cock, he started pounding into me harder, with deep thrusts that wavered between pain and to pleasure.

I closed my eyes, grudgingly enjoying the sensations as Mr. Wolowitz deliberately pumped into me, in and out, going deeper with each stroke. He lifted my legs up higher, rested them on his shoulders and I opened my eyes and looked into his when I began to spasm under him, my orgasm triggering his. I lay there captive beneath him until his orgasm culminated in a long, hoarse cry of release when he trembled and collapsed on top of me. After a few minutes, he pulled out of me, and I remember thinking, "he's gotten his money's worth . . . he'll give me my money now." He didn't.

*****

We dozed for maybe an hour, and I awoke when I felt his hand down between my thighs, pushing them apart and his fingers teasing my clit.

"Ohhhh, Mr. Wolowitz, no . . . I'm sore, please wait. I can't."

Disregarding my whimpering he inserted two fingers inside me and began moving them in and out. He rolled me over onto my stomach and pulling the back of my skirt up began fondling my exposed ass. With one hand, he busied himself playing between my thighs and with the other caressed my ass. He slipped a finger into my asshole, and I stiffened. He continued playing with my pussy and massaging my asshole as he smeared spent cum on and inside it, waiting for me to relax and soften to his touch.

"Your ass is so tight," he said as he pulled his finger almost all of the way out, paused and pushed it back in again.

"I'm going to take your ass, Madison," he said.

"No . . . please, Mr. Wolowitz, don't," but I knew he would do as he wanted with me, even as I said those words.

He pushed his finger deeper into my ass, pass the sphincter ring, and I felt the uncomfortable tightness, and then another finger as he began to stretch and coax me open.

"So tight, so fucking tight," he said in a dry, raspy voice when he pulled his fingers out and gently pressed the tip of his cockhead against my asshole. My body resisted, and I gave a muffled scream into the bed at his violation. He paused and waited for my body to adjust before he again slowly pushed in further. It seemed to go on forever, inch by inch until his cock was completely encased in my dark, warm channel. Finally, with a last thrust, his full length was inside me, and I felt a warm, black shadow descend over me.

After a few seconds, I opened my eyes only to hear myself moaning with increasing pleasure and felt Mr. Wolowitz slowly stroking in and out of me. As I relaxed a little and exhaled, I realized my ass muscles were contracting and releasing around his cock. It no longer hurt, but instead gave me a feeling of fullness and tingling anticipation.

"Oh fuck, oh fuck, fucckk," Mr. Wolowitz, mouthed as he continued to violate my ass. The pain he had initially inflicted had become pleasurable, and when he pushed his fingers into my pussy, the sensations were elevated, and I cried out as my body exploded in an exquisitely intense orgasm. Mr. Wolowitz' thrusting had pushed me flat onto my stomach, and I lay there breathless and sexually sated and with his cock buried balls deep in my ass, he filled me with his thick, copious semen in two hard, deep spurts.

Mr. Wolowitz spooned behind me while he recovered from his orgasm. He kissed the nape of my neck and let his hand leisurely caress my left breast and nipple as his cock softened, pulled free and now lay limp and non-threatening between my ass cheeks.

"You're a good girl Madison, with a fine, fine pussy and ass. Maybe we can get together again," he said as he grabbed a wad of Kleenex and cleaned his cock before pulling his shorts and pants back on.

"A little more experience and you'll be a damn good fuck for some man," he added as he patted my bare behind and climbed into the driver's seat of the cab.

"We'll be in Chico in another ninety minutes or so. I'll drop you off at the Pilot Truck Stop, and you can give your friend a call to pick up you. You think you'll be ok until she gets there?"

"Yes, I'll be okay," I said.

Mr. Wolowitz maneuvered the rig onto Highway 99 from the service road and headed toward Chico. I lay in the back feeling the afterglow of multiple orgasms and my first anal sex. Though it was a little scary at first, I did not regret anything that Mr. Wolowitz and I had shared.

When we got to the Chico stop, Mr. Wolowitz came in with me, and we had coffee and a burger while I called Tiffany. Thank God, she was home. It turned out she had gotten my earlier message and had called the café, but I had already left. She said it would be another hour before she could get here, and for me to stay put.

Mr. Wolowitz and I chatted while he finished his meal and as he stood up to leave, he gave me five hundred dollars.

"You don't need to give me all this, Mr. Wolowitz," I began before he cut me off . . .

"No, I'd give you more if I had it, he said. Who knows, maybe we'll hook up again." I stood up and came into his outstretched arms as he bent and kissed me hard sending those familiar shivers through me before he turned and left.

*****

Despite my having a sore pussy and ass the next day, it was nothing a hot soak couldn't make feel better.

I thought of Mr. Wolowitz often over the next couple of weeks with a little sadness. I found myself fantasizing about him during class, and several times actually awoke during the night having masturbated in my sleep while dreaming about him making love to me. I saw Janice only once or twice after that encounter with her stepfather, and I later found out she had transferred to another college, which meant he had no reason to stop by the campus anymore. I was disappointed at not having seen him again, but as time passed the sensual memories of him lessened and things at school got back to normal.

Then one day while getting ready to meet my boyfriend, I was stepping out of the shower, when I heard someone banging loudly and insistently on the door. Dripping wet, with only a towel around me I hurried to the door thinking it was Mark my boyfriend. Opening the door, I stood in stunned silence; it was Mr. Wolowitz.

"Hello, Madison," he said as he stepped into my dorm room, closing and locking the door behind him.

"Mr. Wolowitz," was all I said, as my towel dropped to the floor, his mouth covered mine and his cock pushed easily inside my welcoming pussy.