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Crossings  

smuttywriter 52T
136 posts
4/1/2021 1:04 pm

Last Read:
4/1/2021 5:12 pm

Crossings


“Welcome to Crossings. My name is Jessica. Are you looking for anything in particular?”

“I’m looking for something special, maybe a one-of-a-kind,” Steve answered, keeping his eyes averted. “It is going to be a birthday present.”

“I know just what you’re looking for,” Jessica replied. “I’ll be right back.”

Before Steve could say anything more Jessica was gone. He was relieved not to have to keep averting his eyes but how could she know what he wanted when he’d not even told her what kind of item he was looking for.

While he was waiting, he looked at some of the strap-ons. He’d heard about them but had never seen one in person. Steve was fascinated with how they connected and made it look like the wearer really had a cock of their own.

“Here you go,” Jessica said as she came up behind him again. Steve turned around and his mouth fell open. She had the pink camisole, a pair of matching panties, a pair of breast forms, and a black wig. He was speechless.

“That’s not what I am looking for,” Steve said when he was able to speak again. “I am looking for a vibrator or dildo.”

“You said you wanted something one-of-a-kind. Now strip so we can see if these lovely things will fit you,” Jessica commanded.

“Excuse me?” Steve replied. He wasn’t sure what sorts of drugs this woman was taking but there was no way he was going to be stripping in front of her then putting on those girly things.

“The door is locked and we’re alone,” Jessica assured him.

“I am not a crossdresser,” Steve protested. He had wondered about it but not enough to try it and certainly not enough to do it.

“Listen boy,” Jessica said in a very commanding voice, “I do not have all day. You will strip now or I will be calling your Mistress.”

“Huh? How?” Steve asked. Jessica held up his cell phone.

“Now strip.”

Steve swallowed hard. He would be completely screwed if she called Miss. Chloe. She had him cornered.

“Please Ma’am, I can’t do this,” Steve pleaded.

“Do you think I’ve never seen a boy with an erection?”

Steve blushed. It was true. He was rock hard and his cock was straining against the front of his jeans. The combination of her words and the clothes were overpowering.

“If I have to tell you again I will call her,” Jessica said sternly as she flipped open the phone to access the phone book.

“Fuck!” he thought. Steve closed his eyes and removed his jacket, letting it fall on the floor next to his feet. He quickly slipped his T-shirt over his head then unfastened and removed his pants, dropping them onto the floor with his jacket. He stood there in front of her with his underwear, socks and shoes still on.

“Everything.”

Steve’s face turned a bright red as he removed his shoes and socks then finally his tighty whities. His cock was sticking straight out and dripping precum. He was so embarrassed but he had no choice.

Jessica set everything down on the glass display case and opened up the package with the breast forms in it. She pulled them out and set them on the counter, then walked around the counter. She rummaged around for a minute then pulled out an electric razor.

“I’m not going to shave your whole chest that will take forever with all that fur, but just enough so that the breasts will stick to your skin. You can finish shaving before you see your Mistress,” Jessica said as she turned on the razor and started to remove his chest hair.

It was an odd feeling but not unpleasant. He had been hairy since junior so it was strange to see his chest bared. When she finished there were two boob-shaped hairless areas on his chest. She used rubbing alcohol to clean the skin then exposed the adhesive and placed them over his nipples. They were heavy and he found himself leaning forward slightly.

“Stand up straight,” Jessica scolded and Steve straightened his back. “Now, put these panties on.”

Steve took the silky panties and carefully stepped into them then pulled them up to his upper thighs. He wasn’t sure how he was supposed to get them over his hard cock. Jessica decided to have some compassion and pressed his cock against his stomach so he could pull the panties up the rest of the way.

Her touch sent shivers through his body and even more precum oozed out of the tip. He was happy the front panel of the panties had a special pocket for replaceable pads to soak up the precum and keep the front of the panties dry.

“Oh, that’s perfect. Your clit is properly tucked out of sight,” Jessica cooed. Steve bristled. He knew he didn’t have a huge cock but it was certainly bigger than a clit. Jessica laughed at his reaction. “Don’t worry boy, when you’re in lacy panties your cock is going to be referred to as a clit—regardless of its size.”

“Oh,” Steve said, then blushed at his lack of knowledge. He prided himself as being someone usually in the know and it was an odd experience to be so out of his element.

“Put this on, being careful not to rip it,” Jessica directed. Steve took the camisole from her and carefully pulled it on over his head. The soft fabric glided over his head and down his body, covering his new breasts and pretty panties. Steve looked down at himself and saw the cleavage then groaned. He blushed and closed his eyes as he lost control and orgasmed, spilling his cum all over the inside of the panties.

“Oh my,” Jessica said then laughed. “When was that last time that happened?”

“About 35 years ago,” Steve said. He was unable to look at her, he was so embarrassed.

“I guess we can forego the wig,” she said then led him to the mirror. “Look at the naughty boy.”

Steve looked at himself in the mirror and blushed again. It was him, but it wasn’t. He cupped the breasts and squeezed them. They felt so real.

“Now comes the fun part for me,” Jessica said. “Bend over that bar and close your eyes. Do not open them until you are told.”

“Yes Ma’am,” Steve walked to the bar and bent over it then closed his eyes. His pantied-ass faced the middle of the room.

Suddenly he felt two hands caressing his ass then the panties being pulled down. He sighed with relief as his cock was able to breath again. The hands massaged his ass then one hand slipped between his legs to with his balls. Steve moaned as his cock started to harden again. The hand that had been on his ass slid around his hip and the fingers wrapped around his cock. “Oh god,” he groaned. When he was fully hard again the hand disappeared then he felt something cold squirt on his ass crack.

“Wait! What are you doing?” he demanded as he tried to pull away. Whoever was behind him, he assumed it was Jessica, slapped his ass hard. Steve had been trained well enough to know that a slap like that meant it was time to behave.

A finger slid through the gel on his ass then pressed against his ass hole. He fought the urge to pull away but failed miserably. The hand fell across his ass again, even harder. Steve cried out in pain and stopped moving. He’d never had his ass played with before and wasn’t sure it was something he wanted. Then again, he’d never thought he would want to be dressed as a woman and he’d already spilled his cum all over the inside of the panties that were now around his ankles.

The finger pressed against his ass hole and slipped into it. Ever so slowly it was pushed further and further in until it was completely buried. “Oh fuck,” Steve whimpered. He was shocked at how it was making him feel. His cock was oozing precum again. The finger stretched the tight tunnel and lightly rubbed against the prostate gland, causing Steve’s cock to twitch.

“Are you ready for it?” Jessica asked from behind him.

“For what?” Steve asked nervously.

“This,” she said and suddenly there was a dildo being pushed into his ass.

“Please … oh god … it is too big,” he groaned. The cock continued to push into his ass until it was completely inside. Then ever so slowly, it started to move in and out. Steve didn’t know what to do or think, all he knew was much more of the anal action and he was going to explode again.

Steve felt someone kneel before him and start to suck on his cock. He moaned then opened his eyes to see who was beneath him. It was Jessica. If she was there, then who was his ass? The cock started to move faster as Jessica deep throated him. Steve tried to keep himself from<b> cumming </font></b>but it was too much for him.

“I’m about to cum,” he warned.

“Cum for me bitch,” Miss. Chloe ordered. Steve reacted to the voice he’d heard say the same thing hundreds of times. He exploded in Jessica’s mouth and his ass tightened around the cock in his ass.

“Oh Miss. Chloe!” Steve cried out as he came more than he had before. His cum flowed down Jessica’s chin and landed on her exposed breasts. When he was done, she stood up.

“Clean your cum off me,” she ordered. Steve licked the cum off Jessica’s breasts as Miss. Chloe pulled the cock out of his ass.

“I think this will do nicely,” Miss. Chloe told Jessica. “You can wrap it all up.”

donsv1962 61M

4/1/2021 2:18 pm

hot

I want to take you into the fiery lair of steamy sexual delight on this hot sultry night.


smuttywriter 52T

4/1/2021 1:04 pm

This is one of my most favorite stories! I hope you enjoy it!


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