Caught In Lingerie

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Young man gets caught by neighbor and leads to sex!
3.3k words
4.64
221.7k
169

Part 1 of the 2 part series

Updated 06/08/2023
Created 12/20/2016
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I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to get home to my dildos. At a red light, I could see my cock growing in my panties.

I was expecting a package in the mail today. It was a sheer pink bra and panty set. I pulled into the driveway and checked the mailbox, but nothing was there. I went into the house and stripped at the door, walking to my bedroom only in my thong. My bedroom was a mess and a sissy's dream. I had a few bras and panties thrown about and the red nightie I had slept in the night before was on my bed. There was a blue mini skirt sitting on the floor at the closet opening along with my heels and the sheer white blouse I had on yesterday. I went to my bra drawer in my dresser and found the matching bra to my thong. It was a 36DD with no padding. I placed my DD inserts in and the nipples poked into the nylon and I LOVED IT! I was getting ready. I then grabbed my white thigh highs with lace tops to make the full sissy lingerie outfit. I got my dildo out and lubed up. I pulled my thong to the side, like a true slut, and worked that cock head into my waiting boypussy! I moaned in ecstacy as I slid down that big eight inch cock! My cock hardened! I raised up and lowered myself onto that big boy cock again and moaned even louder! I was loving being a cock slut! I had been building up for this and was anticipating it all day and I pulled my cock from my panties and gently stroked my sissy clitty and as I felt the balls of the dildo hit my ass and my boypussy stretched to a delight, my doorbell rang.

"Oh no!" I thought. "Who could be here?" I was instantly nervous.

"Did they hear me moan? Will I get caught?" A hundred things were running through my mind. I got off the dildo and put my panties back in place and removed my fake tits. I threw on a pair of sweat pants and a sweatshirt. As I was walking to the door I realized I had thigh highs on and someone would be able to tell, so I slid on a pair of shoes as I got to the door and opened it. It was my neighbor Tim.

"What's up Tim?" I said. I was dreading that it was someone I knew. I'm wearing purple lingerie. A 36DD bra, with matching panties, and thigh highs. My boypussy is wet and my dildo is waiting on my bed for me. How can I hurry this along and get back to where I left off?

"I have some of your mail." he said.

"Mailman put it in my box."

The only thing he was holding was an envelope that was large enough to hold my bra and panty I was expecting today.

"Oh no!" I thought. I think I may have began to get red.

"Is this yours?" he asked.

"Not sure. Let me see." I said. It was addressed to me and I took hold of it and noticed it was open. I looked inside. There it was! My new, sheer pink 36DD bra with the matching sheer bikini panty. I think I was getting more flushed.

"I accidently opened it." said Tim.

"I didn't look before I tore into it."

"I don't know man." I said nervously.

"This ain't mine. Don't know why it has my name on it."

"Listen Charlie" said Tim

"It's alright if it is yours. I won't tell anyone."

"No. This isn't mine." I replied. I was getting more nervous.

"I don't know what this is?"

"Charlie?" he started to look puzzled at me and reached his hand toward my shoulder...

"I can see you're wearing a purple bra now. I know it's yours. It's alright man."

I was frozen. The neck of my sweatshirt was too large and you could clearly see the purple satin bra strap.

"Come in please Tim." I wanted him off of my porch holding my panties and now knowing I was wearing a bra. He came inside and I

closed the door behind him.

"Listen, I can explain. I..." I thought I could tell him something , then he interrupted me.

"I told you that it's alright Charlie. You can trust me. I won't tell anyone.....if you let me see you in your bra and panties right now!" Again, I was frozen. My mouth agape. What was happening? My neighbor just caught me in women's panties and now wants to see me in them.

"What?" I replied.

"You heard me, CHERYL!!!" He began.

"I'm going to call you Cheryl since you want to be a girl. You're dressed in a bra and panties and if I had to guess, you have other clothes too. You probably have garter belts and thigh highs, skirts, dresses, blouses, and heels. Don't you? That's right, I know you do...Cheryl! You don't have to say that you do. I can see it in your face. So, if you want to dress like a girl, I'm going to call you a girl's name, and I want to see you dressed up like a girl!"

He was grinning ear to ear and I was blushing and my cock was getting hard in my thong and becoming difficult to hide in these sweatpants. He had me. He was right. I have all of those things and more.

"OK!" I shouted. I was so embarressed.

"Please stop! I do. I have everything. I love wearing panties and bras and dressing like a girl. It feels so good Tim! I LOVE IT! I love how a bra and panties feel on me. I just love wearing thigh highs with a skirt and blouse and heels. It feels so wonderful! So sexy! It feels so natural to me."

"I knew you did Cheryl. It's ok baby. I can see that you like it. I can see your cock getting hard. What kind of panties are you wearing now?"

"I'm wearing a matching thong to my bra." I told him.

"Wonderful! I thought you might. You are a real sissy! I love that!"

I started to change my mind about this. I quit being afraid and began to get happy and a smerk appeared on my face. I was starting to become more relaxed. He called me 'baby'.

"Now" he said "let me see that pretty little ass of yours in that thong!" I smiled even larger.

"Strip for me Cheryl. Let me see those panties!" I took off my sweatshirt and sweatpants.

"Oh my Cheryl! You look beautiful!" My cock hardened.

"I love the white thigh highs too! You look wonderful! Now, go get those heels. Let me see you in this sexy lingerie!" I turned and walked to my bedroom. Slowly. Trying to move my hips as sexy as I could.

"Yummy! Love that pretty ass in that thong baby!" Tim shouted as I entered my bedroom.

I was coming into another world. A handsome man told me that I looked sexy! I couldn't believe it. I couldn't believe that this was happening. I was getting hard with every compliment he gave me. I was blushing. I could feel it.

I found my heels and slipped my titties into my bra and exited my bedroom.

"OH MY GOD! Cheryl! You are goregous!" I could tell he was sincere by the look on his face.

"Thank you Tim!" was all I could say.

"I mean it!" he continued "You are a beautiful girl!"

I was feeling incredible! All of these compliments were making me sort of high.

"Looks like your sissy clitty is nice and wet!" I looked down and I was precumming and there was a small wet spot in my panties. I was in shock. I was hard and precumming from a man giving me compliments.

Tim was about 5' 11" with short black hair and either 34 or 35. He is in shape, very well built, and weighs about 190. I am 5' 6" and 135 pounds and am 26. I have longish blonde hair down to my shoulders and a slender frame. I had sometimes felt that I should have been a girl. Was this the evidence?

I had been dressing in panties on and off since I was sixteen, but once I moved into my own place, it was all I wore. Then I figured out mail order and in the last four years excessively bought not only panties, but bras, skirts, dresses, heels, garter belts, pantyhose, and blouses. I didn't stop there. I bought the breast inserts and dildos and even had maxi pads and tampons. I wanted to feel what it felt like to wear all of these thing. Feel what they all felt like. Feel what a woman felt like! I had been shaving everything below my eyebrows for two years and Tim noticed right away.

I continued down the hall to the living room where Tim stood. I was placing one foot in front of the other, like a model, to accentuate my walk with a big grin on my face and the heel clicks was all I could hear. I approached him with my nearly see through purple bra and thong with white thigh highs and white heels. He could see my nipples protruding through the bra and the wet spot in my panties was getting larger along with my cock. I was fully hard at six inches. My face was blushing and I felt WONDERFUL!

"Hi Timmy!" I squeaked. "Do you like what you see?"

I walked around him, strutting! Lightly touching his shoulders as I did.

"Cheryl........I.......I...I'm speechless. You look...amazing!" he said. His head kept turning to follow me. He looked me up and down again and again.

"Well, I'm glad you like this. I'm glad you caught me!" I smiled at him.

"Well, since you caught me and you said that you wanted to see me dressed like this....what do we do now???"

I gave him puppy dog eyes and then grinned. I wanted to see if his cock was hard. I was so horny and I had my dildo in my ass less than ten minutes ago. I want to touch his cock and put it inside me! I want to feel him in me!

I walked back around to the front of him and stopped. Our bodies close. My boobs touching his shirt. We leaned into one another and as our lips met I reached to feel his cock and he put his arms around me and pulled me into him. With one of his hands on my ass the other was in the middle of my back pulling me close and I could feel sparks fly inside of me. He was wearing mesh shorts and a t-shirt and I could feel his cock! It was rock hard! Our kiss broke. He held me close and looked at me.

"Cheryl, I want you!" he was gleaming! "I want you now!!!"

"I want you too Timmy. Please take me! Will you make me a girl?" I asked.

"You already are a girl Cheryl! You're a beautiful girl!"

"Thank you!" I said. "I want you too! I want you inside of me!"

I began stroking his cock through his shorts. I don't think he had underwear on. I broke from his hold and grabbed his hand and led him to my bedroom.

As we entered he saw my dildo.

"Cheryl! That's a big dildo!"

"I know. When you rang I had just sat on it. I had it all the way inside of me and I moaned! I thought you may have heard me."

I grinned.

"Now I want you inside of me! I want to feel your hard cock in my boypussy! Make me feel like a woman! I want to make you cum!!!"

"You are such a naughty girl! I love it!" Tim said.

I took off his shirt and then knelt and removed his shorts. His cock was almost rock hard and it sprang right to my mouth. I instinctively opened my mouth and licked the head. I gently grabbed it with my right hand to steady it as I began to tease him with my tounge. I was on my knees as I circled the head with my tounge and then slid it in my mouth.

Tim groaned "Oh god yes!"

I briefly stopped and with his cock partly in my mouth I looked up at him as he looked down.

"That feels wonderful!"

I tickled his balls with my left hand and started to work his cock in my mouth. I was salavating and began slobbering on his cock! I couldn't believe it! I stroked his hot, hard cock while I slid it in and out of my mouth. Deeper each time. I was a cocksucker and LOVING IT!!! I was getting hornier and hornier and sucking faster and faster. Deeper and deeper with Tim moaning all the while. Then I realized I had his whole cock in my mouth! I was in awe! I had tried on a few dildos, but it was nothing like this. I was so turned on by sucking his cock!

"Cheryl! Please stop!" he leaned over and helped me up as his cock slipped from my mouth.

"I don't want to cum. That felt incredible, but I don't want to cum...I want to cum inside of you!"

I stood all the way up and he kissed me again. I smiled and jumped into him and wrapped my legs around him. He picked me up and placed me on the bed. Laying me on my back he broke our kiss and began kissing down my neck. I sighed in relief as he continued kissing me down my smooth, sissy body. Each kiss sending electricity through me with my thigh highs and heels still on, pointed at the ceiling. He had reached my panties.

"Cheryl" I looked down at him

"Look how excited you are! You are so turned on!"

I looked to see my thong was soaked in precum! Tim began to take my panties off. I raised my hips to assist him and my cock let free with strings of precum! He took my panties off and held them to his nose and took a deep breath! I LOVED IT!!! That was such a turn on! I loved that he loved it. He then placed my panties by my face and I could smell them too! They smelled wonderful! They smelled like pussy!

"Cheryl, girls have pussies. Do you know what I do to pussies?" I looked intently at him.

"I eat pussy Cheryl! Then I fuck pussy!" I became giddy!

With that, Tim held the backs of my stockings, at my thighs, and began to eat me out!!! I was in heaven!! I began to moan like a girl! It felt sooooooo wonderful!

My cock was throbing as I screamed

"Oh god, yes Tim!!! That feels soooo good!!! Eat my pussy baby! Oh yeah!!"

He stopped and I looked down at him, between my legs, panting, nearly out of breath. Then he licked my aching cock and started to suck on it! My eyes rolled into the back of my head

"OH YES!!!"

I screamed at the top of my lungs. I'm certain we could be heard. I could only take this for a second or I would cum!

"Tim! Stop. Stop. Stop." I picked his face up off of my sissy clitty.

"Fuck my pussy! Slide that big, hard, cock in me! I want to feel you fuck me!! I want to make you cum! I want to feel you cum inside me!!!"

With that he stood up and pulled me to the edge of the bed. My titties were heaving with every deep breath I took. He found my lube and lubed us both up, slipping a finger in, teasing me! I held my legs in the air, near his shoulders. I felt his cock head press up against my boypussy. He gently eased it in.

"OH FUCK YES!!!" was all I could say.

It was wonderful! It was so much better than my dildos. I could feel his cock inside me! He slowly worked it in. My pleasureful moans led us to where we both wanted to be. After a few seconds he was all the way in!

"I'm all the way in baby! Your pussy feels incredible!" I was beaming with pride!

A goregous man was balls deep in my boypussy and told me how good it felt to him. It felt equally good to me.

I couldn't believe how much better it was than my dildos. I reached down between us and felt him right up next to me. His eight inch cock was inside of me!!! I felt like such a woman!

Tim held my legs out to the side and slowly fucked me for maybe five minutes. Letting me adjust. Each time he was all the way in, I squealed with pleasure! Just like a girl getting fucked. I started to move back and meet his thrusts. They were feeling better and better! He picked up on the pace and slammed into my pussy a little harder each time. Hearing that 'smack' we all know and love. Each time I was moaning louder and louder. Each time he hit my G-spot, I squealed

"OH!...YEAH!...THAT'S!...IT!...BABY!...FUCK!...MY!...PUSSY!"

With his fucking getting harder, my tits and cock (I mean, sissy clitty) were bouncing in unison. Every time he was in to the hilt, I felt close to cumming and I haven't touched my clitty yet. He picked up his speed.

"FUCK YEAH TIMMY! COME ON BABY! FUCK MY PUSSY! MAKE ME CUM!"

I reached for my cock. I tried to stoke it. I could barely with him fucking me! His pace picked up more. I knew he was gonna cum!

"YOUR PUSSY IS SO TIGHT CHERYL! YOU'RE GONNA MAKE ME CUM!"

By now he my lower back off of the bed and was holding my waist, giving him the perfect angle to pummel by boypussy. I looked down and saw my sissy clitty was leaking cum and there was a pool on my stomach.

Our sex was getting hotter by the second! We were so close to cumming! I felt I was going to cum just from him fucking me.

"FUCK YEAH BABY! YOUR COCK FEELS SOOOO GOOD!! CUM IN MY PUSSY!!!"

There it was. That was all he needed!

"I'M CUMMING BABY!!!"

I could feel his body tighten and what I didn't think could happen, did. I felt myself start to cum!

"DON'T STOP BABY! I'M CUMMING TOO!!!" I screamed.

By now only my shoulders were still on the bed and my cock was pointing at my face and as I began to cum my own cum erupted onto my face. I couldn't believe it! One, two, three, four shots of cum hit me! Some shot directly into my mouth. It tasted heavenly. I licked my face and picked up some more of my cum as Tim slowed down and my sissy clitty leaked onto my belly. His cock was still inside of me as he layed me fully back on the bed.

"Cheryl...that was the best sex I have ever had! he said.

"Oh baby! You made me cum so hard. That was incredible!"

He slid he cock from my boypussy and I moved up on the bed. I was exhausted and so was he. He joined me as we lay in our post orgasmic trance.

Here I was covered in cum with Timmy's cum leaking from my pussy, laying in bed with my new lover.

I was a happy girl!

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AnonymousAnonymousabout 1 month ago

Well told, lots of colorful details. No rushing for the first fuck. Charlie/Cheryl was so ready having been lubed up and using a giant dildo. Tim lucked out. Charlie lost his boypussy to Cheryl and, of course, to Tim. I don’t have quite the wardrobe that Cheryl has but do have a few nice things. I have a panty pak of 3 string bikinis that Amazon will deliver today. There’s Paul who lives just a few houses down the street. In the summer I wave at him when I drive by and have seen his abs and strong legs. I’ve gotten off a couple of times when I’m dressed and fantasizing how he would take me. I’m going to order a few things from Temu and Adam & Eve and put my name with his address. Wish me luck!

m1km1n30m1km1n304 months ago

Loved. This.

When you find someone who not only lets you be who you are, and likes you as you are.

This went straight into my Favorites. Thank you!

AnonymousAnonymous7 months ago

Delightful story. Being the Gurl that I am, I've had hundreds of turgid members inside of me. Perhaps thousands, but who's counting. Each have been wonderful. Anywhere, everywhere they could be found. Gallons of seed has been injected into me. Loved every drop. As many as eight loads in one night. I pulsate now with desire from reading this story. Always bareback is the only way for me.

Now that I'm older I only desire someone to speak with and perhaps interact with about this Topic. Dildos are nice but nothing like the real thing..

SissyjohnboySissyjohnboyabout 1 year ago

I’m playing with my clitty now wishing someonewas fucking my boi pussy

AnonymousAnonymousover 1 year ago

wow, wish that would happen to me.

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