The stunning brunette double-checked and triple-checked her makeup at least a dozen times in the bathroom mirror before leaving it to dress. Not less than two hours ago, she had been Linus; however, as each layer of makeup was applied, the male vanished, and Linda appeared, so she no longer referred to herself as a male after that.
She approached the bed, shed her silky flowing dressing, and found the ensemble she had laid out earlier. She took a minute to admire these sensuous garments before fastening the black silk garter belt around her hips and slowly and carefully sliding the black nylon stockings up her legs. She always marveled at the way they made her legs look and feel. Next came the black silk and lace bra that had fake breasts built into the cups, and finally, she stepped into the black silk and lace bikini panties and slowly slid them up.
She ran her hands over her bra and down her stomach and over her crotch. She was getting hard, but there was no time to tend to this need; she needed to finish dressing. The little black dress was shorter and tighter than anything she would normally wear in public, but Dan had purchased it along with the matching lingerie, and she wouldn't disappoint him.
Her hemline was so short that it offered brief glimpses of her lace-topped nylons as she moved and sat down. She thought of changing, but she had promised to wear it to dinner. A few minutes later, Dan knocked on the adjoining room door, and she admitted him. He looked like a million dollars in his dark suit as he briefly checked his appearance. Then, opening the door of the suite, he bowed at the waist and gestured for Linda to enter the hallway where he took his hand in hers, and they headed to the restaurant.
"I can feel eyes on my legs and butt," Linda hissed with a touch of embarrassment and her eyes downcast as they walked across the restaurant.
"Let them look and admire what they cannot have," Dan responded reassuringly as he squeezed her hand. He always seemed to know what to say in these situations.
It wasn't like Linda had not been out in public before dressed and with full makeup, but those outings were usually to a local club that catered to this alternative lifestyle. This establishment was an upscale and well-known restaurant/dinner theater.
They were escorted to a table in the corner where Linda struggled to keep her hemline from rising and giving a show to the waiter who had pulled her chair out for her. She forgot about her embarrassment over cocktails and the excellent dinner that followed. It was as they lingered over their coffee that it happened.
Dan slid his chair closer to hers, gently taking hold of her hand and bringing it to his lips, where he kissed it. He always treated her like a lady from day one. Then, instead of returning her hand to its original position, he held it and moved it under the table and toward his lap. She was told to open her hand, and a second later, she felt his hand help her close hers. When it did, it closed around a thick rope of warm and throbbing muscle.
"Oh my Gawd," she said to herself. "He has his cock out in this fancy restaurant."
"What are you thinking?" she asked Dan in a whisper.
"Blame the way you look in that dress for my condition. I got hard just watching you walk," he responded.
Linda's first instinct was to get up and leave the restaurant, but something made her stay and she gripped Dan's cock a little tighter.
As Linda began to stroke Dan, her mind took a trip down memory lane. Linda or Linus had met Dan shortly after a messy divorce, which just about cost him everything and forced him to move back in with his parents. His cross-dressing was the reason behind the divorce, but that was never made public.
A mutual friend introduced them at a house party he was hosting. Linda, as usual, was dressed to the nines, and they clicked at that first meeting. Later, over cocktails in a quest bar, she told him the truth about her status, and to her surprise, he didn't bolt but moved his chair closer.
Dan had lost a well-paying position when the company he worked for went belly-up and was forced to move back in with his folks. As a result, they had to put their sexual desires on hold because Dan's parents had a rule about no single women being allowed to spend the night, let alone a single man dressed up like a woman. They couldn't use Linda's parents' house because she wouldn't be allowed to dress.
When the unemployment insurance checks commenced, he treated Linus's alter ego to an occasional weekend getaway when both sets of parents stayed in. It presented Linus with the opportunity to get dressed and made up. Dan also began purchasing black silky lingerie for Linda as she loved them, and he loved to see her in them. Nylon stockings, garter belts, and panties in black silk and lace also found their way into her collection, and she loved all of them and soon had difficulty finding someplace to hide all these gifts.
Linda had become more daring thanks to Dan's encouragement in the months they were together, and they were seen everywhere together. Linda was no longer afraid to kiss him in public, but this situation was out of her comfort zone. Now, due to the tablecloth's length and its heavy material, there was no movement to indicate what was transpiring under the table.
"That's it, stroke me, baby," Dan said softly, and Linda complied.
"What happens when you're ready to cum?" Linda asked in a whisper as she continued. "You're going to make me walk out of here with cum stains on my dress or nylons like some cum whore?"

As she continued to stroke him, he reached into his inside suit pocket and withdrew something that he draped over the wrist of her stroking hand, it was a pair of white satin bikini panties.
"Are those new?" she asked.
"Yes, I purchased them for this occasion," he replied. "Now when I tell you that I'm ready to cum just wrap them around my cock and I'll shoot into them."
None of the other diners knew what was happening at that corner table. They only saw a beautiful blonde sitting beside her handsome escort, who had twisted in her seat so his head was closer to his date. They were sharing a conversation for their ears only, and even their waiter had no clue what was happening under the table when he removed their dinner and dessert plates and refilled their coffee.
When the restaurant lights dimmed, it plunged the room into semi-darkness. Linda felt a little better about what she was doing. The stage lights came up, and the show commenced, but Dan and Linda couldn't have cared less.
As Linda continued to stroke Dan's cock she was becoming turned on herself. She felt a familiar fire and hardness begin to build as her silken panties, and she worked hard to will it away.
"Does that feel good, baby?" she heard herself ask Dan in a seductive tone that she had just recently discovered that she possessed.
"It feels great," he replied as he allowed one hand to caress the nylon-covered thigh of the leg closest to him. The feel of his strong, warm hand sliding under her skirt made her hardness return, as he had never done that before, and it excited her.
It was maybe a minute or two later that Dan told her that he was ready to cum and Linda released him for a moment as she wrapped his rock-hard cock in the panties that he had provided before continuing to stroke him with her small hand gripping his cock through the panties.
"Come on, baby," she urged in a low whisper. "Fill up these pretty panties."
Dan leaned back in his seat, and his body shook as he emptied himself into the silky lingerie. Linda could feel his warm fluid shooting out of him and into the panties that she wrapped around his cock. She wrapped the cum-filled panties in a discarded napkin and placed them in her purse. She excused herself a minute later and told him she was returning to their room. She walked quickly, no longer caring how much leg she showed and carrying her wrap in front of her to hide her tell-tale bulge of her hard cock under her tight dress.
About ten minutes later, Dan opened the door to their suite, and once inside, he saw her standing next to the king-size bed, clad only in her black lingerie and heels and looking like a million dollars.
"I want you so bad," she whimpered before approaching him. She then placed her arms around his neck and her lips close to his ear.
"Please fuck me," she cooed into his ear as she pressed her body against his. "I want you to take my cherry."
Dan had no response, as Linda never talked about going beyond kissing and touching.
"If this bothers I'll pull my panties down just enough for you to gain entrance," she told him as she glanced down at her hard cock. Its presence always seemed to prevent him from proceeding beyond touching and kissing.
"It's all right," he replied. "Take them off," he continued as he held her tighter, making sure she could feel his hardness against hers.
"I always wanted you to be my first," she replied in the same seductive purr, taking his hand and leading him toward the bed.
"And I want you to be my first," he answered.
Once there, she assisted Dan in undressing. He had never allowed their encounters to go this far, but with each article of clothing she removed their cocks became harder. He then took her in his arms again and the sensation of his hard cock pressed against hers was beyond belief. As his tongue explored the inside of her mouth she felt his fingers slip between her firm butt cheeks to apply the lube that was on the nightstand to her little pucker.
"Are you ready, baby? " he asked in a low growl as he pulled the bedspread down. Linda mounted the bed and assumed the knees and hands position.
Linda looked over her shoulder and locked eyes with him. "I'm ready," she replied.
She felt Dan place one of his large warm hands on her waist while the other was used to direct his cock toward penetrating her virgin back door. Linda let out a moan as Dan's hard cock slowly entered her.
Dan checked with her every few minutes to see if she was all right, as he had promised to stop if it hurt too much.
Linda experienced both pain and pleasure as Dan commenced to pump her tight ass and she moaned with each of his thrusts. Then without warning Dan placed his hand around Linda's hard cock and began to stroke it gently. Linda moaned even louder. This was a first for him, and she questioned his action.
"I want to make you shoot, " he said into her ear.
Linda's breathing increased as did her moaning yet she managed to tell Dan that she was cumming. A second later, she emptied her load onto the bedspread. It was a moment or two after that she felt Dan place both of his hands on her hips as he increased the speed of his thrusting.
It was a heartbeat later that Dan issued a grunt and emptied the contents of his balls into Linda's tight ass and she moaned with pleasure. As they exchanged gentle kisses while wrapped in each other's arms, they made plans for the rest of the weekend.
Fantastic story. Thanks for sharing kisses Jessicaslims120 💋
Great story, very well written
Oh my god that. Was so well written that it had me so hot and wet. Beautiful story 😘
god i love your stories so much. you really know us gurls well!
Sweet story, and a little naughty, nice 😉
Beautiful start restaurant scene exotic very much a turn on
great intro to these two. might there be more in future?
Good story . I do love to read about someone's " first time " . And , this one was outstanding .
Very nice. How did the rest of the weekend go? That will be hard to top.