Dorothy Surrenders

Written by , on 2024-03-26, genre first times

I must admit, the lady surprised me.

Dorothy was one of those hard nuts -- lovely, sweet, and perhaps a little bit repressed. Although she was thirty, just getting her to hold hands or kiss me (other than a peck on the cheek) took repeated effort. She could be a lot of fun, except for her apparent fear of anything even slightly sexual. But gradually, she had gotten over some of the most basic things: a kiss, holding hands, and the like. Still, there were many barriers we had not yet broken.

Then, one Friday night, she hit me with a big surprise.

We had gone out to dinner at a neighborhood place. I couldn't help but notice that Dorothy, who was almost always prim as a librarian, had left her top button open. It was autumn, so I knew it wasn't because she was too warm.

After dinner, we walked back to Dorothy's apartment. I had my hand around her waist. Her roommate was away for the weekend, so we would have the place all to ourselves.

Dorothy took my hand. We continued to walk together, enjoying the crisp, moonlit night. I stopped her under a tree and we kissed. She smiled.

Soon we arrived at Dorothy's door. She opened it and we stepped into the apartment. Immediately, she gave me a big, wet kiss. Usually her kisses were sweet and gentle, but this was the most passionate kiss she had ever given me. I took off my windbreaker.

Dorothy put her hands on my waist and pulled my shirt loose. Her hands were under my shirt. I held her closely and slid my hand down to her butt. This was something she had never allowed before, but this evening, I got no reaction except a sweet smile and an even more passionate embrace.

Our bodies were pressed very close to each other. I'm sure she could feel my bulge beginning to form. I slid her skirt up and put my hand on her butt directly.

We sat down on the couch. Both of us kicked off our shoes. Dorothy just stared at me for a few seconds. She was licking her lips. I noticed that she was blinking.

Now Dorothy took off her sweater. She smoothed her blouse. She leaned in and kissed me. I noticed her hand on the inside of my thigh.

"Dorothy," I said, "what is going on here?" Again we kissed. I pulled her to me. She undid one button on my shirt.

Dorothy giggled. "Why do you ask?" she said. I put my hand on her knee.

"This isn't like you," I said. I began to fondle her earlobe. "Not that I'm objecting." She chuckled.

She smiled as she spoke. "I had a dream," she said. "I dreamed that I had sex with you."

"Was I good?" I said jokingly.

"Silly," she responded with a smile. She gave me a peck on the cheek. "I had it five nights in a row."

"Five nights straight?" I said. She smiled and nodded. "I must have done something right." Dorothy laughed.

"It surprised me so I prayed about it. A lot," Dorothy said.

"What was the answer?"

"Surrender, Dorothy," she said.

"Was there a green-skinned witch involved?"

"No, silly," she replied with a laugh as she unbuttoned another button on my shirt. "I prayed on it several times and I kept getting the same answer."

"And what was it?"

She had a cockeyed smile on her face. Her tone was chipper. "You're the one."

Dorothy blinked as she undid another button on her blouse. Her cleavage was very visible. I leaned over and kissed it. She jumped.

I reached inside her blouse and unhooked her bra. Dorothy smiled. Then I kissed her neck.

Her pupils got very wide. I could feel her jump just a bit. She was giggling softly. With that, she unbuttoned her blouse fully.

"You're sure this is what you want?" I asked.

Dorothy frowned.. "Don't you want to?" she asked as she unzipped my pants.

"I just don't want you to wake up in the morning thinking, oh my God, what did I do?" I said. In silent reply, she unhooked my belt.

"You're sweet," she said. "Thank you." Now her blouse slid off. I kissed her cleavage. She moaned softly.

Eagerly, Dorothy unbuttoned my shirt. 'You make me feel attractive and desirable," she said. "I've never felt that before."

"That's because you are attractive and desirable," I said. She smiled. She kissed me.

Taking my hand, Dorothy eagerly led me down the hall. "I've been waiting for this," she said softly, almost to herself. I smiled knowingly.

We sat on Dorothy's smallish bed and again we kissed. Now she removed her bra. I sat there for a moment, looking at my otherwise prim girlfriend topless.

Dorothy smiled. She leaned in and kissed me. I stood up and took off my pants.

Moving around in back of her, I cupped Dorothy's bare breasts in my hands. I began to play with them. I could feel her nipples hardening. She sighed.

I blew in Dorothy's ear. My hands on her waist, I slipped her skirt off her. She turned to me and pulled off my shirt.

"Black," I said, barely audibly, as I noticed her black panties.

"I've heard black is sexy," she said, blinking. She smiled.

I lay on top of her, kissing her hard. My tongue worked in her mouth. She seemed to enjoy it. "Mmm, I like this," she almost whispered.

We felt each other's almost naked bodies. My hands explored Dorothy as hers moved all over me.

As we came together, I noticed that her panties were thoroughly soaked. My hands went to her waist and easily slid her panties off. She leaned in and kissed me as she removed my underpants. I began to kiss her naked body, up and down.

Moaning, Dorothy began to kiss my bare chest.

I lay beside Dorothy, my fingers in her wet but tight pussy. I put one finger in, then another. She smiled and kissed me. I led her hand to my stiffening cock. Softly she began to stroke it.

Suddenly, she sat up and turned her back. "I...I don't know," she said.

"What about your dream?" I said. I kissed the back of her neck. I heard her sigh.

"Dorothy, please don't to this," I said. I began to kiss her down her bare back.

"I guess I'll be going, then," I said.

Dorothy turned. "Please don't go," she said softly. I wrapped my arms around her. She kissed me hard. I placed my hand on her pussy. She grinned. Again I blew in her ear. She threw her head back. With a sigh, she flopped on her back. She gave me a smile.

"OK," she said.

"Whenever you're ready," I whispered.

She kissed me. "Be gentle," she said softly.

Again I rolled on top of her. "Of course, my dear," I said. "I'll take care of you." Dorothy smiled and sighed.

"OK," she said.

"I've never wanted anyone as much as I want you. I've wanted you ever since I met you."

She smiled coyly. "I know," she said softly.

As I first tried to enter, she had her legs too tight and almost blocked me. I kissed her.

"If you're not ready..."

"Oh, I'm ready!", Dorothy exclaimed. "I'm ready!"

With a big kiss she spread herself wide and I entered. It was a rough entry; she was very tight. But with a few pushes, I managed to get in. Once inside, I pumped, slowly and gently at first, but then more vigorously as we went along. She began to loosen up..

"Ooooh," she moaned. I pushed deeper and deeper. I couldn't get enough. I kept going, harder and faster.

Dorothy had a big, wide smile. It was clear she was enjoying herself. I could see and feel the blood all over her sheets.

"Oooooh!" she screamed. "Ohoooh yes!" She was happily jiggling underneath me. Our bodies were moving in sync.

Dorothy grabbed the sheet tightly. Her eyes got really wide. She wrapped her arms around me as I continued to thrust my stiff cock further and further into her previously unexplored pussy.

"Oh, God!" Dorothy screamed. "Oh, God!" I rammed her more forcefully. She bit her lip. She was beginning to perspire just a bit. So was I.

" GOD!" Dorothy screamed. She was breathless. I went in harder and deeper, picking up speed as I went. Dorothy's breath was getting very short. Her eyes got wide.

"Oh YES," she said. "YEEEEESSSSSSS!" I continued to push into her, harder and harder, deeper and deeper. Dorothy closed her eyes. She seemed like she was about to explode.

Finally, I popped, spewing into her. She simply lay there softly, letting the flow enter her sweet body.

"!" she shrieked again. She was shivering with pleasure. She was shaking all over. When it had stopped, she kissed me yet again. I rolled off her. I had a big smile.

"Was it good for you?" Dorothy asked.

"Yes, great. You're already good at this. And you?"

Dorothy was smiling widely. "Great," she said. "Really great! I didn't expect it to be so good. Wow!" She gave me a big kiss.

"How are you feeling?" I said.

Dorothy grinned. "Wonderful," she replied. We lay together for some time.

The next thing I remember is the sun poking through the bedroom window.

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