Curious but Willing

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Ian flipped me on my side next to him, spooning me, his cock slipping between my thighs and into my crack. I could feel the wetness and the throbbing of his cock. My heart raced.

"You sure?" Ian mumbled into my ear as he dry humped my crack. "I mean, being your first time and all."

"Ian. I've been curious for suck a long time. It took a whole lot for me to take this step. Can't I go all the way?"

"Fuck me, Steven," Ian exclaimed. "You have no idea what it's going to be like, I mean taking it up your butt."

"I'm willing to try," I confessed.

Ian got up and turned me onto my back, pulling my legs apart and leaning on top of me. I felt his weight as he lay on me. His cock slid under my balls and his abs pressed on my hard cock. We kissed. I had to admit that Ian was a hot kisser. Not that I'd had any experience with man-kissing, but I could tell how kissing the way Ian did it struck all kinds of chords in my body.

I felt his cock head prodding my hole. Instinctively, I shuddered and squeezed my ass shut. He kept the prodding, gently, waiting for me to relax and get used to being stretched. I squirmed under him.

"You're so hot, baby," Ian said as he prodded my hole, applying some pressure. "Relax and open up for me. Let me make love to you."

I tried to help. But I felt like it wasn't under my control.

Placing his arm around my neck, his other hand clutching my raised thigh, Ian thrust and entered.

I screamed. The pain was excruciating. I felt like I'd been ripped.

"Easy, easy, easy," I kept repeating, trying to catch my breath as my hole screamed with agony. Ian stopped the pressure, keeping his knob just inside my rim. I gazed into his eyes and brought my hands onto his chest, rubbing on the lion tattoo, spreading his sweat over his hairy chest. Somehow, this made me relax. His naked hulk on top of me caused me to ease up my ring muscle. Ian must have felt this, and he thrust, pushing his shaft in. I had no way how much cock was already inside me. But I knew that I was stretched to the maximum.

Slowly, the pain started to recede. The feeling was incredible. I raised my head and reached for Ian's lips as felt more hard cock force its way into me. Ian moaned into my mouth. "I'm already halfway in, baby."

Halfway in? This couldn't be. Oh my God, there was more cock to invade my insides. I reached down to grab his butt cheeks. Firm and rippling. I pressed on them.

"Want more?" he teased. "You can't be green, Steven."

I was trying to control my breathing, to relax around the shaft stretching me. I was barely able to speak. "You're fucking a virgin ass, Ian," I finally managed to say.

With a loud grunt, still gazing deep into my eyes, Ian thrust hard. I screamed some more as I felt his rod bury, as if penetrating another hole inside me. This time, I felt his thick bush against my balls as he pressed and grinded on me.

Dropping down on top of me, slobbering on my mouth, Ian grinded. "Fucking intense, baby."

My arms reached up to wrap around his neck as I felt his cock slide out, then push back in, slowly, tentatively, as if he was trying to find his way into my bowels. I squirmed and ached for more.

"Fuck me, Ian," I squeaked.

Ian fucked me. His thrusts were hard and deep, changing his speed rhythm from fast thrusts with a part of his shaft going in and out, to slow and deep, making me take the whole of his dick, sucking it in.

It couldn't have been more than a few minutes when Ian raised himself on both arms and started pounding with force, panting and sweating and grunting.

His explosion inside me was massive. Incredibly, I could feel his squirts filling my tunnel, his cock pulsating with wanton pleasure. He kept cumming like forever, and I kept squeezing on his cock base forever. Finally, he dropped back on top of me, his tongue and lips all over my face, his dick buried deep inside my body.

With a sigh of regret, I felt Ian's cock slide out of me. Following it was a stream of cum, seeping out onto my thighs, dripping down on the couch. I reached down, embarrassed that I was sliming his place, and tried to catch some of the cum squeezing uncontrollably out of my stretched hole. Ian laughed reaching for a box of tissue.

"Here," he snickered. "Baby, that was the biggest load I have ever shot."

Again, I felt proud. My own dick had gone limp during the fucking. But I didn't care. I had brought such pleasure to this man, and my own pleasure was out of this world.

I had to leave. As I walked back to my place, some 30 minutes away, I felt the soreness of my ass with every step, and I reveled in it. I had taken cock. And it had been amazing. Ian had made a bottom out of me, when all during my adult life I'd been topping. He had controlled me and had taken me only in the way a real man could take another human being, female or male.

I contemplated my situation. This experience could have turned sour. I could have been picked up by someone else who wasn't as sweet and incredibly hot as Ian. I could have been raped. Or injured or attacked or beaten up. Instead, I had turned bottom for the most beautiful top ever. Ian had pulled me up in his arms and we danced naked and covered with sweat and semen, kissing and grinding. His cock was hard, pressed against my belly, even after he'd shot two big loads. When I offered to suck him off again since my ass was too sore for more fucking he turned me down saying that he had to keep some for our next time. This meant that I now had a boyfriend. I snickered at myself. Even in my imagination I had never considered the situation that I was in now.

But, really. Had I turned gay? If sucking cock and taking it deep up the butt wasn't gay, what was? I was pink gay. As pink as a stick of cotton candy. Pink, and fluffy, and sweet. Maybe not fluffy although one might consider my body hair as fluffy. Ian had called me sweet. So there. Yes, I was gay and a bottom at that, and I had to live with that. Or better yet, change my life accordingly, with a boyfriend and all.

I got to my place, shed off my dirtied clothes and showered. I jacked off with Ian's image in my head, and the soreness from his cock in my ass. I shot jets of cum.

When I got into bed, my phone rang. Ian. It was already 2 o'clock in the morning. He'd turned his cam on and was lying naked on his bed, his cock rock hard, his smile incredibly killing.

"Hey, babe," he greeted me, his white teeth glaring at me. "I was thinking of you, and look what that had got me." He moved the cam down his hot body and at his cock. It filled my phone screen and I moaned out loud. This beautiful member had been in my throat and inside my ass.

Ian laughed fisting his dick. "Yeah, babe. I want you to moan for me."

"Come over," I begged. "Ian, come over and take me again."

Ian came over and the night was sleepless, painful, and heavenly.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
18 Comments
AnonymousAnonymous9 months ago

OMG I love this story I so want to be in Stevens place with a hot hairy sexy guy like Ian. Obviously there would need to be tons of lube for my first anal sex but oh my god at 57 I need to experience this for the very first time so so bad. I love sucking cock & swallowing cum & if a man is clean I really enjoy eating his ass but I need the next level of taking cock up my hole.

AnonymousAnonymous9 months ago

Great story and I loved the internal dialogue. Very real

AnonymousAnonymousabout 1 year ago

I thought it was fucking Hot made me want to stroke my cock all7inches and HARD

AnonymousAnonymousabout 1 year ago

Hot story

Modest7Modest7about 1 year ago

Very sexy enjoyed this one but wish it was longer

Show More
Share this Story

Similar Stories

Prostate Awakening Straight man discovers anal pleasure with two men and a bet.in Gay Male
First Time with Neighbor Daddy 18-year-old boy is taken by older neighbor.in Gay Male
Taken for the First Time Ch. 01 An older man takes a willing first timer all the way.in Gay Male
Boyfriend Gets It in the End She convinces boyfriend to try out his hung friend.in Gay Male
Friend's Father During a long weekend at a friend's, his father takes me.in Gay Male
More Stories