Caught Wearing a Bra! Pt. 02

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

"Uh, well, you see, uh, I've never done this and uh, well, I'm pretty nervous," he stammered. "Um, well, I hope everything works like it's supposed to."

Sandra smiled and held her arms out to him.

"Don't worry about that, sweetie," she said softly. "I'll lead you through it. But if earlier was any indication, you'll do just fine. Now, put your arms around me and kiss me while you unhook my bra."

Mike put his arms around Sandra and unhooked her bra while they shared a deep kiss. Sandra put her arms around Mike and unhooked his bra and they dropped them on the floor at their feet.

Sandra sank to her knees, stopping to gently bite and lick Mike's nipples on her way down. She hooked her fingers in the waistband of Mike's hose and panties and pulled them down his legs. His hard 4" cock, still sloppy from when he came in his panties, jutted at her face, a gleaming drop of pre-cum trying to drip from the slit in the end.

She took his mushroom head into her mouth, then pushed her lips down until her nose was against his smooth shaved pubis as she continued to work his hose and panties down his legs. Without taking her mouth off of his cock she managed to get the garments off of his feet and he was naked.

Mike put his hands on her head and ran his fingers through her hair while he enjoyed the first time in his life he'd had his dick in a woman's mouth. He knew he couldn't let her suck on him for very long lest he blow his load in her mouth.

Sandra swirled her tongue around his shaft, savoring the musky cum from his earlier orgasm and the salty flavor of his sweat and pee from the long day of wearing the hose and panties under his slacks. She loved running her hands up and down his soft, smooth legs while she had his hard cock in her mouth.

Mike pulled her head away from his crotch. "You have to stop," he gasped. "I'm afraid if I cum now I won't be able to get hard again!"

Sandra sat back and smiled. "Okay. I'll stop, but only because I want you hard when you fuck me."

Sandra stood up as Mike sank to his knees. He hooked his fingers in her hose and panties and pulled them down to her knees. He pushed his face into her crotch, inhaling her sexy musky scent, then pushed her back on the bed.

He stood and pulled her still wet hose and panties down past her knees. Sandra raised her feet and let him take them off of her.

Mike pulled her feet to his face before he took her hose off. He sniffed and licked her feet and toes, enjoying the musky scent of hosed feet that had been in pumps all day. When he dropped the hose and panties on the floor beside the bed he again pulled her feet to his face. He ran his tongue across the bottoms of her toes, then put both her big toes in his mouth. Sandra moaned, and her hips moved when she felt his tongue on toes.

Mike worked his mouth up her legs, licking her calves, feeling the stubble of hair. Sandra pulled her knees back and spread herself wide as his face neared her dripping pussy. Mike could see her lips spread open and the wetness clinging to them.

He licked her lips while he inhaled the scent of musk, piss and sweat from a pussy that had been in panties and hose all day. This time he could see her swollen clit, pink and jutting from the folds of skin at the top of her slit. He leaned in and sucked the bud into his mouth.

"Oh, oh, oh!" Sandra yipped when she felt his lips and tongue on her sensitive clit. She wanted to grab his head and hold it there until she had another orgasm. But she wanted something else even more.

"Come up here and fuck me," she hissed, pulling his face away from her crotch.

Mike moved on top of her, rubbing his body against hers. When his lips were on hers he could feel her hard nipples against his chest.

Sandra reached between them and smiled when she felt that Mike's cock was fully hard. She positioned his bulbous head at her opening. "Now push," she whispered in his ear as she wrapped her legs around his thighs.

Mike groaned when he pushed his hard cock into a wet pussy for the first time. He'd tried to imagine what it would be like for years, but it was much better than he ever imagined.

He groaned again when he started to stroke his dick in and out of Sandra's pussy and realized that he was going to shoot his cum into her any second. He'd so wanted to be like the actors in the porn movies he watched and fuck her in different positions for what seemed like hours.

He wanted to stop it, but he couldn't. His body stiffened. He held his throbbing cock as deep in her as he could. He felt tears and shame as he felt his dick throb and pump his cum into her just seconds after he pushed it in.

Sandra knew what was happening. She'd wanted him to last longer, but wasn't surprised considering it was his first time. She put her arms around him and hugged him to her.

"Oh, yes, baby!" she moaned. "Oooh, yeah, just like that! Give me all of your cum, baby! Ohhh, that feels so good!"

Mike collapsed on top of her, his face buried in her shoulder.

"I'm sorry, Sandra," he said quietly, trying to not cry. "I was afraid that would happen. I'm so sorry."

Sandra rubbed his back gently.

"It's okay, baby," she murmured as she kiss his neck and ear. "I loved it. I love knowing your cum is in me. Let's snuggle and get some sleep now."

"Will it get better when I do it more?" he asked her.

She smiled at him. "Well, there's only one way we can find that out. I'm willing to find out if you are!"

Mike smiled and pulled her to him, his sloppy cock laying against his thigh and her ass.

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
11 Comments
SissyBoy1WarszawaSissyBoy1Warszawa27 days ago

You write wonderfully the story of Mike and Sandra, their experiences at work and then a hot date ending with wonderful sex. Will this lead to an emotional closeness between Mike and Sandra? What will happen at work, will Mike's boss use his secret? 🧑🏻⚧️❤️👩🏻👙👨🏻

ps. Sorry for any mistakes and linguistic inaccuracies, I don't speak English.

Best regards, SissyBoy from Warsaw, Poland. 👩🏻‍🦳⚧️❤️👧🏻🧒🏻

AnonymousAnonymous27 days ago

I'm almost 70 I think what has happen in your story is every cross-dresser's dream to find a woman who doesn't mind seeing a man wearing lingerie and nylons. I would suggest you put a sanitary napkin in your panties for accidents that way you won't be wearing wet panties. It's not that hard to carry a spare in case you need one. I look forward to the next chapter.

PetaThePantieBoyPetaThePantieBoyabout 1 month ago

I absolutely loved this story and can't wait to read more of your stories. As you can tell from my screen name I wear panties 24/7 and wear nighties every evening after work. I also wear a bra with my breast enhancers. I have ALWAYS wanted to be with a woman while wearing my feminine clothing but it has never happened, and at the age of 68 and no longer able to achieve erections, I doubt that it will ever happen, but I can enjoy reading stories like this. I can still masterbate and have a lttle bit of an orgasm just not very much fluid anymore. I am so looking forward to reading more of this and other stories of yours.

Norahjoy67Norahjoy67about 1 month ago

I liked it because there was so much I could relate to

Sissyjackie2008Sissyjackie2008about 1 month ago

loved this story. My mom knew i dressed and we would have girly weekends when dad was away on business. One day she ordered a pizza and told me I was to answer the door. She wanted to see me flirt with him a little and gave me tips. I was so scared, but did it. She smiled when he left and told me i was a little minx.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Lost Suitcase Adventure Lost bag & friend's clothes fit better than her husband's.in Transgender & Crossdressers
Feminized by Girlfriend A curious boyfriend gets feminized by his girlfriend.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Adele finally becomes a Sissy Caught dressed as Adele.in Transgender & Crossdressers
Teacher Surprise College student bumps into his high school teacher at a club.in Transgender & Crossdressers
More Stories