tagAnalCindy's Finger (& Her Strap-on)

Cindy's Finger (& Her Strap-on)

bythomstevens©

It all began when Cindy stuck her finger up my ass. She was running her tongue lightly up and down the shaft of my cock, but paused for an instant to gauge my reaction. I moaned slightly, appreciatively. It felt good. She smiled and began slowly moving her finger in and out.

We were naked on her bed in her apartment on a Saturday morning, the sunlight streaming in through her bedroom windows. At first, I wasn't fully awake, although Cindy did a fine job of waking me up. She had started nibbling and nipping at my balls before moving up to my cock. And now she had a finger up my backside. I was awake and she had my full attention.

It wasn't the first time that a girlfriend had stuck a finger up my ass, but this was different. Cindy wasn't stopping at one. She began working a second finger inside me and then a third. She stopped and looked up at me as she slowly fucked me with her three fingers.

"How does this feel?"

"Hmm," I moaned to myself. "Feels wild. Strange. Really good." It felt so full and warm. "Don't stop."

"Oh no," she said smiling. "I am just getting started." With that she took my cock in her mouth and starting sucking in rhythm with her fingers pumping in my ass. I didn't last long. Between her mouth and her fingers, the orgasm was shattering.

She cuddled up next to me and began kissing my neck. Then she whispered, "Have you ever been fucked in the ass by a woman?"

I was startled, "Ah, no." I paused. "Nor by a man either."

She laughed. "That much I figured. You are too straight to swing both ways. Suggests a lack of imagination, you know."

It was my turn to laugh. So, I was too straight. Well, we are what we are. Cindy was bi and had broken up with a long-term girlfriend just before we met. She was my first bi girlfriend, or at least the first that I knew about.

I looked into her eyes, a lovely shade of hazel. They seemed to smile back at me.

"Well then, have you ever fantasized about a woman fucking you with a strap-on?"

Wow, I thought. "Can't say that I have. I know, a failure of imagination."

With that she rolled over on top of me, held me down by the shoulders and gave me a long and passionate kiss. Then she sat back, still holding down my shoulders. For her size, she seemed suddenly very strong. She had a wicked smile on her face and a wild look in her eyes.

"I really, really want to fuck you with my strap-on"

I wasn't sure what to a say, so I said the first thing that came to mind. "I didn't know that you had a strap-on"

"I have two," she said her smile growing wider. "Wanna see?"

"Sure," I replied, amazed how we just went from imminent sodomy to show-and-tell.

She hopped off me and went into her walk-in closet. In a few minutes she came out wearing a black harness and a not overly large dildo which was, somewhat incongruously, blue. She had a big smile on her face and wiggled her hips, making the rubber cock swing back and forth.

"This was in the last of the stuff I picked up from Nina's. What do you think?"

What did I think? I wasn't sure what to think. I knew that she had gotten the last of her things from her girlfriend's apartment, but had no idea that sex toys were in the box. Clearly I still had much to learn about Cindy.

She stood there, beautifully naked, except for the harness and the swinging blue rubber cock. The goofy grin on her face made it all seem playful and silly. Kind of sexy. Then again, the cock felt more than a little threatening, especially given its intended destination.

Could I handle it? Physically? Emotionally? Would it be liberating or emasculating? Was my masculinity all that fragile that it could be shattered by a blue rubber cock? Should I grab my clothes and run for the door or bend over and submit?

As I was considering my options, I realized that my cock was voting in the affirmative. Given that I had cum just a few minutes before, the erection was impressive. Perhaps, I was overthinking the situation. Best to go with my gut, or in this case, the guidance provided by my cock.

"I think you look very sexy," I finally replied.

"So can I fuck you?" she asked, putting an extra emphasis on the hard percussive "f" of fuck. It was both a question and a challenge.

I took a deep breath and said, "Sure."

She raised an eyebrow and stepped next the bed, holding the rubber dildo so that it was pointing straight at me, inches from my face. Then in a tone I didn't expect she barked, "Suck my cock, boy!"

I started to suggest that that wasn't really necessary, but, as I opened my mouth to speak, she shoved the blue dildo down my throat. She grabbed the back of my head with her other hand and pulled me forward.

The dildo wasn't that long, but I gagged as it hit the back of my throat. My eyes started to water and I jerked my head back against her hand. She pulled the cock back but kept fucking my face. Now that I could breathe, I started to get in the rhythm and began to move my head to meet the cock, taking it deep, but not enough to gag. She moved her hand from the back of my head to caress my cheek and said softly, "Good boy. Suck that cock."

I am not sure how long she fucked my face, but I sort of slipped into the surreal vision of a blue rubber cock being shoved down my throat while watching Cindy's breasts bounce slightly as she thrust her hips toward my face. Then suddenly, she stopped.

"You're a good little cocksucker, now aren't you?" she said with a evil grin. "Get on your hands and knees. Now we'll have some real fun."

I did as she directed, got on my hands and knees on the bed. I wasn't sure what to expect. Given how rough she was fucking my face, would she come at my ass like a battering ram?

Instead, she walked away to the bathroom. I heard water running and soon she was back with a warm washcloth which she rubbed against my ass.

"Gotta have you kissing sweet," she purred. She got up on the bed and leaned forward, kissing and licking my backside. She ran her tongue up and down my perineum, licking my scrotum and then flicking across my asshole. Then she sank her tongue in my ass, fluttering around and then stabbing in and out like a tiny cock. It felt warm, exciting and relaxing at the same time.

I heard her squirt lube and felt the cool wetness as she worked one lubricated finger into my ass, and then another and another. She slowly finger fucked me as I groaned happily.

"If you like my fingers, you are going to love my cock." She gave my ass a hard swat pulling me out of my revery.

"OK, roll over on your back, ass on the edge of the bed, a pillow under your hips. I want to see the look in your eyes as I fuck you."

I got in position. My knees were spread, my asshole slightly elevated. I have never felt so exposed and vulnerable. She stepped up between my legs. Her eyes seemed to burn with raw lust.

I felt the cock press against my asshole. Rather than ramming it in, as she had my mouth, she was very gentle, easing her way in the puckered gateway. The blue cock was much bigger than her fingers, but slid in smoothly. I closed my eyes and gasped at the blend of sensations - pressure but not pain, a sense of complete surrender, of submission, and the simple joy of losing control.

She began to move in and out, slowly at first, but then fast and faster. Soon she was fucking me hard, slapping my ass with her hips as she drove the cock into me, then pulling most of the way out before slamming back again. The strap-on jabbed hard across my prostate creating a feeling that was brand new - intense, and pleasurable yet almost painful.

It was overwhelming, too much and not enough. I couldn't take it and I wanted more. I found myself croaking, "Fuck me, Cindy. Fuck me." And she did. Harder and harder.

Cindy slid one hand down the top of the harness and rubbed her clitoris. "Jerk-off," she commanded. "I want to see you come."

The sensation of having my ass pounded by the strap-on merged into the sensations as I jerked my cock to life. The stimulation of my prostate as the dildo slammed into it were as powerful as the pleasure from my hand jerking the shaft and glans. I watched as Cindy grew closer and closer toward her own orgasm.

Suddenly, if was all too much and I came. Cum splattered on my belly as the world seemed to explode. Cindy kept driving into me with a manic frenzy, until she opened her mouth in a silent scream and her whole body began to shake. She slumped forward slightly with the strap-on still buried inside me. In a few minutes, she stood again and pulled out. I felt oddly empty.

She took off the harness, dropped it on the floor and climbed onto the bed. I was still gasping for breath. She cuddled next to me.

"So how was it?"

"Amazing." I ran my fingers though her hair. "Can we do that again?"

"Sure." she relied. "Next time, maybe I'll use the bigger dildo."

"Oh no," I said, feigning horror. "Let's practice more with the blue one. That one is big enough. I won't be surprised if my ass is plenty sore tomorrow."

"Maybe so. Will it have been worth it?"

"Absolutely," I replied.

I turned and kissed her, then whispered in her ear, "You can fuck me in the ass any time, my love."

She gave me a wicked smile. "An offer I shall not refuse."

Report Story

bythomstevens© 7 comments/ 40012 views/ 55 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartgoodlooks, naughtyboy4yourstrapon and 53 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by krug01/08/18

Great Start

Great Start
I hope you continue with more adventures between these two

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous01/07/18

Interesting story

Many women can be inspired by this story. Cindy uses good technique and language to initiate dildo training. She is now in charge of relationship and will enjoy it to the max.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Failedscout01/07/18

Very Nice

Very Enjoyable Read.

Thank you for writing and posting here.

Last anonymous questioning strap-on is obviously more than a little dumb.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous01/07/18

Not one but two

She just happened to have two strap on toys.
He is too straight to swing.
Then all of a sudden poof he wants it up his ass!
Good grief man get a life.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by ptebaden01/06/18

Too short

I wish you write much more

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 7 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel