My girlfriend, Aisha, had always been a little shy in bed. We’d been together for eight months, and while we had great sex, she was still hesitant about trying new things. I, on the other hand, had a bit more experience — especially with anal.
For weeks, I’d been gently bringing it up. Not pushing, just planting the idea.
One night, after we’d both had a couple of glasses of wine, I finally asked her directly while we were lying in bed.
“Have you ever thought about trying anal?” I asked softly, my fingers tracing circles on her stomach.
Aisha went quiet for a few seconds. Then she turned her face into my neck and mumbled, “I’ve thought about it… but I’m scared it’ll hurt.”
I kissed her forehead. “We don’t have to do anything you don’t want. But if you ever want to try, I’ll go really slow. I promise.”
She didn’t say yes that night. But a few days later, while we were making out on the couch, she suddenly whispered against my lips:
“I want to try… with you.”
My heart started beating faster.
That weekend, I made sure everything was perfect. I bought good lube, got a small beginner plug, and made sure we had the whole apartment to ourselves. I wanted her to feel safe and relaxed.
We started slow, like we always did. Kissing, touching, taking each other’s clothes off. I went down on her first, licking her until she came on my tongue. She was already wet and sensitive when I reached for the lube.
I looked up at her. “We can stop anytime, okay?”
She nodded, biting her lip. “I trust you.”
I started with just my fingers, using plenty of lube. Aisha was nervous at first, but she slowly relaxed as I gently worked one finger inside her. I took my time, kissing her thighs and whispering how beautiful she looked.
After a while, I added a second finger. She moaned softly, her hips moving a little.
“Does it feel okay?” I asked.
“It feels… weird,” she admitted, “but good weird.”
I kept going slowly until she was comfortable. Then I reached for the small plug I’d bought. It was smooth and not too thick.
I covered it in lube and gently pressed it against her. “Breathe for me, baby.”
Aisha took a deep breath as I slowly pushed the plug inside her. She gasped when it slipped in, her body tensing for a moment before relaxing again.
“How does it feel?” I asked, kissing her inner thigh.
“Full…” she whispered. “But I like it.”
I smiled and moved up to kiss her. While the plug stayed inside her, I went down on her again, licking her clit until she came hard, her legs shaking around my head.
After she caught her breath, she looked at me with glassy eyes.
“I want more,” she said quietly.
I raised an eyebrow. “You sure?”
She nodded. “I want you to fuck me… with the strap.”
My stomach flipped with excitement.
I got up and put on the harness, choosing our smallest dildo — still bigger than the plug, but not too much. I made sure everything was well lubed before positioning myself between her legs.
Aisha was on her back, legs spread, looking both nervous and turned on.
I leaned down and kissed her deeply. “Tell me if you want to stop.”
She nodded.
I pressed the tip of the dildo against her ass and slowly pushed forward. Aisha’s mouth fell open as I entered her, inch by inch. She was incredibly tight, and I had to go extremely slow.
“Fuck…” she moaned, gripping the sheets.
I stopped halfway. “You okay?”
“Don’t stop,” she breathed. “Keep going.”
I pushed in the rest of the way until my hips were flush against her. We both stayed still for a moment, letting her adjust.
Then I started moving — slow, deep strokes. Every time I thrust into her, Aisha let out these soft, desperate moans I’d never heard from her before.
I reached down and rubbed her clit with my thumb while I fucked her ass. Her whole body was trembling.
“You’re taking it so well,” I whispered. “My good girl.”
That seemed to do something to her. Her moans got louder and she started pushing back against me.
“Harder,” she begged.
I gave her what she wanted, fucking her a little faster while still being careful. The sound of skin slapping and her moans filled the room.
After a few minutes, I felt her body start to tense up.
“I’m gonna cum—” she gasped.
I rubbed her clit faster and kept thrusting. Aisha came hard, her ass clenching around the strap as she cried out. Her whole body shook with the orgasm.
I slowed down but didn’t pull out right away. I leaned down and kissed her gently while she came down from it.
When I finally pulled out, Aisha was breathing heavily, looking completely blissed out.
She looked at me with a shy but satisfied smile.
“…I think I like anal,” she said.
I laughed softly and kissed her.
“Good,” I whispered against her lips. “Because I’m not done with you yet.”
Aisha was still catching her breath when I leaned down and kissed her softly. She looked completely fucked out — cheeks flushed, lips swollen, and her legs still slightly trembling.
I gently pulled the strap-on out of her and watched as her stretched hole fluttered, a thin string of lube and her wetness dripping down.
“You okay?” I asked, brushing her hair out of her face.
She nodded slowly, then gave me a shy but satisfied smile.
“I… really liked that,” she admitted quietly.
I smirked. “I could tell.”
I got up and removed the harness, then climbed back onto the bed. Aisha was still lying on her back, looking at me with those big, innocent eyes. But there was something new in them now — curiosity mixed with lust.
I ran my hand slowly down her body and stopped between her legs. She was still wet.
“Turn over,” I said softly.
Aisha hesitated for a second, then rolled onto her stomach. I grabbed a pillow and slid it under her hips, lifting her ass up. She looked so fucking good like that — face down, ass up, completely exposed.
I reached for the lube again and poured more onto her already slick hole. She shivered when the cold liquid touched her.
I didn’t put the strap back on yet. Instead, I pressed two fingers against her entrance and slowly pushed them inside. Aisha moaned into the pillow.
“Still sensitive?” I asked, moving my fingers in and out slowly.
“A little…” she mumbled.
I leaned down and kissed one of her ass cheeks, then the other. Then I spread her open with both hands and dragged my tongue over her hole.
Aisha gasped loudly.
“Oh my god—”
I licked her slowly, circling her rim with my tongue before pushing it inside. She tasted like lube and sex. I could feel her trying to stay still, but her hips kept twitching.
I reached under her and rubbed her clit at the same time. Within minutes, she was moaning again, pushing her ass back against my face.
I pulled back after a while, my chin wet.
“You want more, don’t you?” I asked.
She didn’t answer with words. She just nodded into the pillow.
I put the strap-on back on — this time choosing a slightly bigger dildo. Not much bigger, but enough that she would feel the difference.
I got behind her and pressed the head against her hole. Even though we’d already fucked once, she was still tight. I had to go slow again.
Aisha let out a long, shaky moan as I pushed inside her. This time I didn’t stop until I was buried all the way in.
“Fuck… it’s bigger,” she whimpered.
“I know,” I said, gripping her hips. “You can take it.”
I started fucking her with long, deep strokes. Every time I bottomed out, Aisha let out these desperate little sounds that went straight to my clit. I reached around and played with her pussy while I fucked her ass, and soon she was dripping onto the sheets.
I picked up the pace, fucking her harder. The sound of skin slapping filled the room.
“You like getting your ass fucked, don’t you?” I growled.
Aisha moaned loudly into the pillow but didn’t answer.
I grabbed her hair and pulled her head back gently.
“Answer me.”
“Y-yes…” she gasped. “I like it…”
“Say it properly.”
“I like getting my ass fucked,” she moaned, louder this time.
I slammed into her harder. “Who’s fucking your ass?”
“You are— fuck— you are!”
I kept pounding her, one hand on her hip and the other rubbing her clit fast. Aisha was shaking beneath me.
“I’m gonna cum again—” she cried out.
“Cum for me,” I ordered. “Cum with my cock in your ass.”
Aisha came hard, her whole body seizing up as she screamed into the pillow. Her ass clenched tightly around the dildo, milking it as she came. I didn’t stop moving until she went limp beneath me.
I slowly pulled out and took the strap off. Aisha was breathing heavily, her face buried in the pillow, completely spent.
I lay down beside her and pulled her into my arms. She immediately curled into me, hiding her face in my neck.
After a few minutes, she finally spoke.
“…I didn’t know it could feel that good,” she whispered.
I smiled and kissed the top of her head.
“We’re just getting started,” I said. “Next time, I want to train you properly.”
Aisha lifted her head and looked at me, cheeks still pink.
“Next time?” she asked softly.
I smirked and slid my hand down to squeeze her ass.
“Oh yeah,” I said. “We’re going to make sure this pretty little hole gets used to taking cock. Maybe even train you to take bigger ones.”
Aisha’s eyes widened slightly, but I saw the way her thighs pressed together.
She was already getting turned on again.
I leaned in and kissed her slowly, then whispered against her lips:
“But for now… get on your knees. I’m not done using you tonight.”
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