Steve opened the door to Crossings and quickly stepped inside. His heart was racing as he pulled off his sunglasses then tucked them into his jacket pocket. As his eyes adjusted to the dimly lit store, he nervously ran his fingers through his graying hair.

Crossings was a small shop in the basement of an old office building in downtown Syracuse that sold lingerie for men and other cross-dressing specialty items. They also carried a wide variety of toys, including one of the largest collections of strap-on toys in the area.

Steve looked around and was happy to see he was the sole shopper. He didn’t even see a sales clerk, which made him even happier. Having a sales clerk hovering over him would’ve made him even more nervous.

As Steve made his way to the ‘toy room,’ he paused to look through some of the lingerie. He was there to get Miss. Chloe a new toy for her birthday but it wouldn’t hurt to do some window shopping while he was there. After all, he would never actually wear any of it.

He lightly fingered a silky pale pink camisole with delicate white lace trim. It was so soft and feminine. Steve blushed when he realized he was starting to be turned on. “It’s only because you’re picturing Miss. Chloe in it,” Steve thought to himself.

Happy with his excuse, he moved onto the stockings and shoes. He never would have believed there were so many different kinds of stockings—regular, fishnet and thigh-highs in a dozen different colors. He loved seeing Miss. Chloe in them but couldn’t imagine wearing them himself.

He moved to the shoes and his size. Steve traced the heels on a pair of five-inch tall stilettos that were his size then put them on the floor. He slipped his sock-covered feet into them and groaned in pain. His calves protested against the muscles being stretched in this new way and he quickly stepped out of them He returned them to the shelf and continued on to the ‘toy room.’

Steve stepped through the curtains that divided the two sections and found himself surrounded by hundreds of cocks of various lengths, thickness, colors and materials. He’d never seen so many in one place before.

“Damn,” he muttered.

“Impressive, isn’t it?” a feminine voice said from behind him. Steve spun around and came face-to-face with a short plus-sized woman with long red hair, brown eyes with gold flecks and huge breasts. She was wearing a tight-fitting black dress with a plunging neckline that showed off most of her breasts.

“Yes, it is,” Steve answered and quickly looked at the ground.

“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 a breasts 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 in the middle of a store then putting on those girly things.

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

“I am not a cross-dresser,” 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 phonebook.

“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.


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 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 later,” 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 high 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 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 25 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 play 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. 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 fucking his ass? The cock started to move faster as Jessica deep throated him. Steve tried to keep himself from cumming but it was too much for him.

“I’m about to cum,” he warned.

“Come 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 fake 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.”

Jessica winked at him then went to the cash register to ring all the items up.

“You may stand up and turn around Stephanie,” Miss. Chloe said to Steve. He stood up and turned around. “Oh, how lovely! I should have done this sooner.”

Steve blushed as his mistress caressed and played with the fake breasts. She smiled then kissed him.

“Now that is a birthday present! Thank you so much,” Miss. Chloe said. “Change back into your other clothes and give the stuff to Jessica to put in a bag. Then we’ll go home and we can have my favorite birthday sex.”

Steve smiled and quickly undressed then pulled on his regular clothes. He was so happy Miss. Chloe had taken his anal virginity. They’d talked about it before but it had never happened.

“$235.13 please,” Jessica said. Steve handed her his credit card and watched as she slid it through the machine. A few minutes later, she handed him a slip to sign. Steve finished the transaction and picked up the bags.

“Happy birthday Chloe!” Jessica said as she hugged his mistress.

“Thanks Jess,” she replied then led Steve out of the store.

When they got home Steve gave Miss. Chloe the best birthday sex ever, then they talked about him spending more time dressed as a woman. That night Steve fell asleep a very happy man.

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June 2018
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