Randi's First Date

byTravel_by_day©

Roger prepared for his transformation as butterflies filled his stomach. He had transformed hundreds of times before but this was the first time that someone would be seeing him in person.

As Roger took a bath and shaved his body to remove all traces of hair, he thought back on what had brought him to this point. As far back as he could remove, Roger had loved dressing up in women's clothes. As a child he used to sneak into his sister's room and try on her things. He had to stifle his desires in high school, but once he started college, he would often go to classes wearing a bra and panties underneath his clothes, a practice that he continues to this day as a 27 year old accountant.

Since graduation and moving out on his own, Roger has had much more freedom to dress up. Roger had a closet full of women's clothes, and after getting back from work every day, he enjoyed putting on makeup and getting fully dressed up.

About six months ago, while searching for tips on how to look more feminine when he dressed up, Roger stumbled across a website that included a chat room for transgendered, cross-dressers and admirers. Roger signed up, using the name Randi. In addition to the supportive discussions with other cross-dressers, Roger also started to frequent the erotic chat section. Dressed up in his finest lingerie, Roger enjoyed chatting with men as Randi. Roger had never been with another man, but found himself turned on by the thought of men wanting him dressed as a woman.

Randi started chatting frequently with a few specific guys. One of the guys was named Hugh. He was smart and funny, he seemed a really nice guy but he could get very racy when chatting. Hugh sent a picture to Roger and it turned out he was good looking too, so Roger decided to send Hugh some pictures of "Randi" dressed up in a red bra and panty set, with a black and red corset, red stockings and a pair of 6 inch red heels. Roger was a bit of a portly guy, but when he put on the corset it gave him a very voluptuous shape with a nice bosom with a slimmer waist and round ass. Roger had done up his face with make up and was wearing a long, blonde wig.

"Great pictures," Hugh emailed back. "I'd love to see you in person in that get up. I'm coming to your city in a couple months for a conference. What do you say we get together when I am in town for some fun?"

At first, Roger wasn't sure how to reply. It was one thing to talk about sucking and fucking a stranger on the internet, but a whole other thing to have some there in person, especially seeing as Roger had never been with a man before or had a cock in his mouth or his ass.

Before responding, Roger went out and bought a dildo. Before deciding anything, he wanted to know what it felt like to be entered by a dick. Roger got dressed up as Randi and took the dildo out of its box. He practiced sucking on it. Physically he was able to suck on it, but Roger was finding it really didn't do much for him.

Roger decided to see what it would feel like in his ass. Roger put a condom on the dildo and lubed up the dildo and his ass. He started off with a finger and then another one to work open his butthole. It felt good to have the fingers working inside him Once his ass felt open enough, Roger inserted the dildo. It was painful. Roger tried for a minute, working the dildo slowly in and out of him, but it didn't feel good.

"Forget this, there's no way I'm going to have a dick in my ass," he said.

Just then Roger caught sight of himself in his bedroom mirror. He saw Randi in the mirror, dressed in a beautiful black bra, black corset and a black thong, the strap of the thong pushed aside so the dildo could enter his ass. The sight of this beautiful blonde getting a dildo in her ass turned Roger on, and soon he found his cock growing inside his thong. Roger started to think of how hot it would be to be a beautiful blonde pleasing a man, and soon the pain disappeared, replaced by a desire to have a cock inside him.

Roger emailed back Hugh and agreed to meet him when he was in town in a couple of months. During that time, Roger decided to commit himself to practicing with the dildo to make sure he was ready for Hugh's real dick when he arrived. Now that day had arrived.

Roger stood up from the bath and dried himself off. He moisturized his skin and move to his bedroom to get ready to transform into Randi. He put make up on his smoothly shaven face. He got dressed in an all-blue outfit. He started with a blue corset with white lace trimming. Once the corset was in place, Roger put on a blue, lacy bra and a blue set of silk panties with white lace trimming. Roger slipped on a pair of blue silky thigh-high panty hose and a pair of black heels. Finally, Roger put his blonde wig on his head.

Roger looked in the mirror and saw the beautiful Randi looking back at him. Transformation complete, Roger became Randi, and Randi was sure that Hugh would enjoy seeing the smooth, white skinned blonde when he arrived at the apartment.

Randi went into the living room and got ready for Hugh's visit. She had a bucket of sparkling white wine chilling in a bucket by the couch. Randi put a porn DVD with voluptuous women masturbating. She turned down the lights and lit a few candles.

A few minutes later, the apartment buzzer went off. Randi buzzed in Hugh and unlocked the door. She took a seat on the couch, laying back seductively and crossing her panty-hose covered legs.

About a minute later there was a knock on the door. "Come in, it's open," Randi said.

The door opened and Hugh walked into the apartment. He was even better looking in person than his pictures had indicated. Hugh was tall with brown hair and blue eyes. He was thin and well dressed. When he saw Randi sitting on the couch, a gorgeous smile came over his face. He walked over towards Randi.

Randi pointed at the wine chilling in the bucket and said, "do you think you could open that up and pour us a couple of glasses?"

"Certainly," Hugh said. Hugh was impressed at how feminine Randi looked and sounded. Randi was speaking in a soft voice, and Hugh found it very sexy.

Hugh popped the cork on the sparkling wine and poured two glasses of wine. He handed a glass to Randi, and then they clicked glasses. Hugh and Randi both took sips of the wine, and then Hugh sat down on the couch beside Randi. Hugh reached out and stroked Randi's leg.

"Do you like what I am wearing," Randi asked.

"Mmm, yes, very much," Hugh said, allowing his hand to creep along Randi's inner thigh. Randi shivered at Hugh's touch. She found herself starting to get excited. The cock inside her blue panties started to grow.

Hugh's hand reached Randi's crotch, and he used his fingers to start to stroke Randi's taint. Randi leaned her head back and moaned. She closed her eyes and ran her hands down her body. She felt Hugh's lips on her leg, starting to kiss her just above the knee. His hand continued to massage between her legs. Randi's hands reached down, and she started to stroke her growing cock through the fabric of her panties. She was soon hard as a rock.

Hugh's lips worked their way up Randi's leg. He reached the top of her hose, and started to run his tongue along the elastic of the blue pantyhose. Randi reached into her panties and started to stroke her hard cock, still keeping the panties on her.

Hugh grabbed Randi's legs and spread them apart. He put his face into Randi's crotch and started to kiss her balls and taint through Randi's panties. Randi loved the feeling of stroking her cock against the fabric of her panties while Hugh's mouth worked on her balls. Randi had been saving herself, not masturbating for two days, and quickly she felt an orgasm build up inside her.

Randi moaned and released herself into her panties. The come came streaming out, so much that it soaked right through her underwear and created small, white bubbles of semen on the outside of her panties. Hugh moved his mouth up from Randi's taint and balls, and started licking and sucking up the come from Randi's soaking wet panties.

Once Hugh had sucked up all of the come he could, he moved up and started kissing Randi on her lips. Randi could taste the salty come on Hugh's lips. Randi parted her lips, and Hugh's tongue entered her mouth.

Randi and Hugh kissed for a few minutes. Randi could feel the bulge in Hugh's pants pressing against her leg.

"Would you like to move to the bedroom?" Randi asked. Hugh didn't respond verbally, but instead picked Randi up in his arms and walked with her to the bedroom. Hugh threw her on the bed, and started to undress. Hugh pulled off his pants and boxer shorts, and his cock sprang straight out. Randi quickly grabbed the cock and took it in her mouth. She could taste the pre-cum on the tip of his cock.

Randi licked the shaft of Hugh's dick, moving down until she could suck on his balls. Hugh moaned as Randi's lips and tongue worked on his ball sack. Hugh let Randi suck on his balls for a moment, but then grabbed her head and guided it back up onto his cock. Randi took the full length of Hugh's penis into her mouth, and started pumping up and down on his cock. Hugh moaned with pleasure at the feeling of having the warm, wet mouth of the beautiful blonde working on his penis.

Randi was loving the feeling of having the cock in her mouth. While she had been comfortable with having the dildo in her mouth when practicing, the dildo in her mouth had never really done much to excite her. Sucking on a real cock, though, was turning her on very much. The heat of it, along with the occasional taste of the pre-cum made it feel different, and knowing that she was pleasing a real person made the emotion of the event monumental. It made Randi wonder what a real cock would feel like in her ass.

Randi didn't have to wonder for long. Hugh pulled his cock out of her mouth and turned her over, pulling her panties off her ass. Randi opened her leg and spread open her ass cheeks with her hands. Hugh knelt down behind Randi and started moving the tip of his penis up and down Randi's ass crack. Each time the tip of Hugh's cock would reach Randi's asshole, Hugh would insert the tip, just a little bit at first, before pulling out and running the tip away from her hole. As this continued, Hugh started pushing his dick a little more into Randi's asshole, until, finally, her ass opened and swallowed his cock.

Hugh pushed himself deep into Randi. Randi looked up and saw herself in the mirror on all fours, with Hugh stationed behind her. Randi's blonde hair fell down over her face. Hugh's hands were on the side of Randi's ass as she watched his hips pump back and forth. Hugh was looking down at his cock entering Randi's ass.

Randi found it very hot. She looked almost like a porn star, getting fucked by a stud from behind. She found her cock growing as Hugh continued to pump inside her. Soon her cock was rock hard, banging against her stomach and Hugh moved in and out of her ass.

"I love it! Fuck me, stud. Fuck me like a porn star slut," Randi cried.

Hugh grunted and then said, "Oh yeah, take it, you horny little porno slut. You love hard cock, don't you?"

Randi just moaned and nodded her head, pushing herself back onto Hugh's dick. Hugh started pumping in and out of Randi's ass quicker and faster. He moved one hand up to Randi's shoulder and started using it as leverage to get deeper and faster into Randi.

"Oh God," Hugh cried. He pulled his cock out of Randi's ass and started to stroke his cock, keeping the tip close to Randi's asshole. Just as he was about to come, Hugh put just the tip into Randi's ass, and released his load of come into her. He pulled his dick out, and looked at the come dripping out of her asshole. The come ran down onto her balls.

Randi and Hugh collapsed on the bed and kissed. Randi could feel the come running out of her ass and down her ass cheeks. Randi loved the feeling of it.

Hugh had to leave for a business appointment. Randi showed him to the door, kissing him on the way out. Randi put back on her panties, which were now crusty with her come. She sat on the couch and thought over the day, and how great it felt to have pleased a real man. Randi walked over to her computer and checked her account on the TG/TV board. She was ready to make a few more appointments with some of the other guys she was chatting with. Randi definitely wanted to have the opportunity for some future dates.

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