Caught In Lingerie Ch. 02

Story Info
Sissy boy used again...and loves it!
1.6k words
4.66
63.2k
59

Part 2 of the 2 part series

Updated 06/08/2023
Created 12/20/2016
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right now! My pussy was still wet from the cum and the lube. I could feel it and I felt like such a whore. I slipped from Tim's arm and slid under the sheet. I thought I'd wake him pleasantly by sucking his dick. I wanted him hard and back inside me!

I couldn't believe how I was feeling. Just 35 minutes ago my sexy neighbor was cumming in me as I was cumming on myself and now I wanted more! I loved it! I was a sissy slut for cock and loving how I felt.

Under the sheet I began to play with Tim's dick. It was a bit limp, but I was determined to fix that! I started to lick it and caress it with my tongue. He began to harden slowly, but I kept playing with his cock and like a talented slut, I quickly had it totally hard and pointing to the ceiling. I was on my knees, under the sheet and the blowjob was getting louder since I was salivating over his man meat.

I stopped for a second to catch my breath and looked down at my clitty and I was precumming on the bed. Just a little, but there was no doubt that sucking cock had made me hard and had my sissy clitty leaking! My inner slut was really coming out and I was totally fitting the part. I was in heaven! I began to feel like a woman. Women make their man happy by blowing them and get wet from just that so I was fulfilling my role. I was horny and wet; I was Tim's woman! Just then Tim lifted the sheet.

"Well hello beautiful!" he said as he looked down at me.

My eyes met his. "Hi baby!" I said after I pulled my mouth off of his cock and held it in my right hand, covered in my saliva and a drip of precum oozing from the tip.

"What are you doing?" he asked with a smile, teasing me.

"We dozed off and I thought I'd wake you from your nap." I grinned.

Then I held his cock and licked its head with my tongue keeping eye contact and catching that precum.

"OH YES CHERYL!!" he exclaimed as he let his head roll back.

I knew he liked it. He couldn't hide it. I continued working his meat. Bobbing my head up and down, deep throating him. I was getting better! Tim was now fully awake and was enjoying my new found talent. He spread his legs and let me in between to work on him. With every pleasing moan he let out, I knew that I was doing my job!

I would go slow, fast, tickle his balls, then take a break from sucking and jerk him and lick his balls, occasionally stopping to make eye contact with him and let him know I was enjoying this as well and to see his reaction to my skill.

I wanted to make him cum in my mouth. I wanted to let him know how committed I was to him. I wanted to be his cum slut! I wanted to taste his cum and savor and swallow a load, but I was so horny that I had to put that hot, hard, precumming, wet cock in my pussy. I had made his cock hard and I wanted to feel it explode inside me!

"God Cheryl, this feels so good; I can't believe how you can suck my dick! This is the best blow job I've ever had!"

I was so happy with that. He just told me that I was better than a woman at sucking dick. I couldn't believe how horny it made me!

I knew he wasn't go to last much longer, but I wanted to prolong it. I broke off from my suck job and ripped the sheet off of us as our heat was building. I straddled him, then grabbed his face and made out with him like I was a horny school girl. His hands searched my body. Grabbing my ass and feeling my tits. I moved my hips up and down, letting his cock slide around my body, searching for my hole.

I broke our kiss and told him "I want your hard dick in my pussy."

Not waiting for an answer, I leaned back and grabbed his cock with my right hand. I could feel it throbbing in my hand. It was so hard and hot! I guided it to my waiting boypussy and slid it in.

I worked the head in, closed my eyes, and threw my head back

"Oh my God, YES!"

I let go and put both hands on Tim's stomach. I gyrated my hips and worked the length of his cock inside me.

"Oh GOD!! YOUR COCK FEELS SO GOOD!!" I screamed.

I opened my eyes to see Tim looking at me, grinning like a devil.

"Your pussy is soooooo tight baby!" he tells me.

With that, I have the whole length of his massive meat inside me. I'm now resting on his pelvis.

I take a second and relax, realizing that for the second time in an hour I have my gorgeous neighbor's hard cock inside of me! I'm still wearing my white thigh highs and purple nylon bra with my 36DD fake titties slid in. My sissy clittty is hard as a rock and a stringy drip of precum makes its way to Timmy's stomach. He can see how excited and happy I am.

"That's it baby, work my cock in your pussy!" he says.

I take it slow at first and get his entire length inside me.

"Your dick is soooo big baby!" I tell him.

I make small motions at first to loosen up again and get used to the size of his cock. It feels so good! I just sit and grind on him.

"That's it Chery, ride my pony!" he tells me.

With that I begin to move my hips up and down and his cock slides in and out, massaging my pussy. Each time I move up a little farther and let more of his dick out, just so it can go back in. I can feel every vein in his throbbing cock as it enters me!

Timmy holds my hips, helping me up and down. He then pulls me down to him for a deep, passionate kiss and all the while I never stop riding his cock!

We break the kiss. I get more and more comfortable and begin to pick up the pace. I raise up and let myself slide back down his gorgeous manhood. Every time he gets balls deep I moan like the slut I've become; I'm in sissy bliss!

"Bounce on my cock!!" He says.

That was all the encouragement I needed. I begin to bounce like a pogo stick on him, leaving just the head of his cock inside of me and slamming back down, burying his dick in my warm, wet, boycunt. Each time squealing like a slut. My titties and sissy clitty bouncing in unison with the ride!

"OH...GOD...YES...YES...YES!!"

I thought I was going to cum each time I impaled myself.

"Your dick is so big and hard baby! I LOVE IT!!"

"That's it slut! Tell me how much you like my cock in your pussy!"

"I LOVE YOUR BIG, HARD DICK! I LOVE YOUR COCK IN MY PUSSY!! I WANT YOU TO CUM IN MY PUSSY! FUCK ME BABY!! FUCK ME!! MAKE ME CUM WITH YOUR COCK!"

With that my lover grabs my tits and thrusts up, meeting my rhythm. Our fucking is getting faster, louder, and harder. I can't keep this up for long. I'm going to cum; I can feel it building.

"That's it Timmy! Keep fucking my pussy! Don't stop! I'm gonna cum!!" I yell out as I bounce up and down.

"Me too baby! I'm gonna cum in your pussy!!" He says.

As soon as he said 'pussy'...that was it! My sissy clit exploded on my boyfriend's belly. Nearly simultaneously I could feel his cock pulsing, twitching in my boypussy.

We each slowed down and I just sat on him. His dick still inside me. My clitty still hard, dripping cum. The both of us are gasping for air, out of breath.

"That was amazing Cheryl!" he said as he looked at me.

"Oh my God, yes!!" I answered as I grind my hips on his.

I don't want to get off of his cock, but I know I have to. I lean into him for a kiss and let myself off of him. I lick my cum off of his belly. I can feel his cum leaking from me, again! I feel so slutty! I crawl up next to him to kiss him again.

"Cheryl, that was incredible!!" he tells me.

"I know! I don't want you to leave." I tell him

"Who said I had to leave?" he replies.

"Want to stay for dinner then?" I ask.

"Only if you are the desert!" he says.

"We'll see!" I grin.

I feel so satisfied. So relaxed. So happy knowing that I just pleased my man. I just had the greatest sex of my life for the second time in two hours!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousabout 1 month ago

Part two is equal to or better than Part 1, Enuf said.

PS to Cindy: keep those dreams, it’ll happen for you. You deserve to feel good.

4Leather4Leather2 months ago

One could only dream of that happing.

AnonymousAnonymousover 1 year ago

I wish it had been me xxx

cdCindy1cdCindy1almost 4 years ago
wonderful story

This is a great follow up to the 1st chapter. It shows that someone like me, a sissy faggot cocksucking CD, can start to fall in love with his male lover. This story is wonderful and made me feel so good.

Please tell us more stories. This one is fantastic.

Hugs & kisses,

cdCindy1

AnonymousAnonymousalmost 6 years ago
Most men

Love the thought of giving or receiving cock . I've been on both ends of the act. I like it both ways.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
More Stories