Dan's landing a new job temporarily ended his availability for getaways, as working on weekends was mandatory. Linda, or rather Linus, understood, and to compensate, they spent hours on the phone or laptops planning their next rendezvous. She didn't use her webcam because she couldn't dress for him while living at home and never wanted him to see her sans makeup and lingerie.
Her suggestions of what she was going to do to him were made in a breathy voice and were enough to get him hard, and more than once, he masturbated as she talked to him. Their patience paid off, and before they knew it, Dan was given a weekend off. Because of his dedication and attention to detail, he was rewarded with a Friday off with pay. Upon hearing this, Linus, aka Linda, took that Friday off from her his/her job and made the two-hour drive to their favorite hotel after breakfast.
He paid for adjoining rooms and left a key at the desk for Dan and headed upstairs. Once inside, he commenced the long and involved process of becoming Linda.
Dan arrived a few hours later and headed to the empty adjoining room where he showered and changed into his lounging attire. He knocked on the door that joined the rooms, and Linda, looking like a million dollars, opened the door. She wore a black sheer floor-length nightie over a black bra, garter belt, and nylons. She greeted him by kissing him deeply and then stood back to allow him to enter.
"I have something for you," she said, pointing to the table.
On the table was a beautiful white box tied with a black ribbon and bow. Dan carefully opened it, and his heart skipped a beat as he viewed the contents: nylons, a garter belt, panties, and a shiny black bra similar to Linda's. Dan began to feel uncomfortable as he examined the lingerie. Wearing her panties while pleasurable was a spur-of-the-moment event, but now his little t-girl had purchased a complete ensemble and expected him to wear it.
"They are beautiful," was all he could manage to say.
"They will look even better when you wear them," Linda said. "But first things first."
She bade him sit in the desk chair after she had him strip, draped a barber's cape around his shoulders, and placed a mesh cap on his head
"You need to look the part before you dress," she added, pulling various brushes and makeup containers from her train case and applying them to his face. As she worked she would occasionally brush her hard cock or her fake silk covered tits against his body.
Dan had second thoughts and almost jumped out of the chair; however, something made him stay. Slowly, the gentle touch of Linda's brushes and sponges worked their magic, softening his hard, masculine features. Any reservation he had vanished when Linda placed a long, brunette wig on his head and styled it before she removed the cape, allowing Dan to stand. The anticipation of what was to come had him as stiff as steel, and he became even harder as she dressed him.
First, Linda placed the black and lace bra around his chest and inserted padding into the empty cups, which gave him a more feminine appearance. Next, a high-wasted garter belt was placed around his waist before he asked to sit again, and Linda provided instructions on how to don the nylon stockings and attach his nylons.

Finally, the tiny bikini panties were slid up his nylon-covered legs and the sensation caused his hard cock and heart to jump. A sheer black nightie, similar to what she wore, was handed to Dan, who placed to over his head and allowed it to cascade down his body.
Linda then took him by the hand and led him to the closets off the main entrance, as they had mirrored doors. Standing next to Linda, he looked like another girl. They embraced and kissed with a long, deep kiss that included a tongue. When they finished, Linda gently pushed him back and then spun him around before embracing him again. When she did Dan felt her hard cock hidded under the silk and lace push against his ass.
"Oh, baby," she crooned as she placed her hands on his waist, "I want you so bad."
" I want you too," he replied, not believing what he had just said.
"Get on your hands and knees," Linda requested before darting into the bathroom.
Dan did as his lover requested, and a moment later, she was pushing his nightie to his waist and slowly sliding his panties down. A heatrtbeat later he felt Linda's fingers applying a slippery substance to his anus pausing only to apply a coat her her hard cock.
"Are you ready for me, pretty girl?" Linda asked.
Dan had no answer as he was confused. He had always considered himself an alpha male or a man's man, and now here he was dressed and made up like a girl. Had spending so much time in Linda's presence changed him? He stole a sideways glance at himself in the large mirror, and he saw a moderately pretty girl in sexy lingerie staring back at him and he saw his lover remove her nightie and panties to reveal a very hard cock and then kneel behind him and just like that the confusion passed.
"Yes, I'm ready," he heard himself say in a quiet voice.
"Now relax. I promise not to hurt you, and I will stop if you tell me," Linda added.
Linda placed on hand on Dan's shoulder and took hold of her/his hard cock with the other and commenced to guide it in Dan's butt. Dan expected intense pain but was surprised at how little it hurt. The mirror's reflection showed a sexy girl with a hard cock fucking another pretty girl in the ass.
Dan's cock became hard at the sight and he moaned softly, which caused Linda to increase her movement.
"Are you OK, pretty girl?" Linda asked.
"I'm OK," he answered.
A moment later Linda announced that she was going to cum and with a sexy moan she emptied herself into Dan. She had just removed her cock from Dan's butt when he managed to place Linda on her back and press her nylon covered knees against her boobies.
He wiped his ass with his hand and covered his cock with the reminents of the sex lube that she had used on him and mounted her pushing his still hard cock into Linda's boy pussy causing her to moan with pleasure. It didn't take long before Dan announced that he was going to cum and Linda urged him on.
As they lay on the floor exchanging gentle kisses, they knew that their getaway weekends would never be the same.
