Hi, I'm Vanessa Lynn Wilson. I'm a lifelong crossdresser/sissy since age 10, when I snuck down to the basement and slid into a pair of my older sister's pantyhose. This story is part fact and part fiction. You decide which is which. Please let me know what you think at VLWillinois2@gmail.com
Vanessa spent all day preparing for her date with the other crossdresser she met online. She picked out her best possible outfit from her modest collection of women's clothes that she had accumulated over her years of dressing. She chose a black, satin blouse with lace-up sleeves and a red knit skirt. She chose a pair of sheer black pantyhose (her absolute favorite article of women's clothing) would look great with the black patent leather four-inch platform heels. Vanessa tossed some assorted items of make-up, including the sexy red lipstick into a bag. She also added a very fragrant floral perfume and several packages of condoms. Feeling satisfied that she was ready, Vanessa headed out the door dressed as the guy everyone knew her as.
As she drove to the nearby hotel, she could hardly believe her long-time fantasy was soon to become reality! Kimmy, like Vanessa was also a married man living the traditional role as husband and father. However, he also had an "inside she" who was waiting to play. Vanessa found herself drawn to Kimmy because of the feminine side Kimmy possessed.
Other straight, gay and/or bi guys Vanessa met online tended to be too aggressive, too impatient or way too hung up on a CD/TV being passable as a woman. Kimmy was friendlier, sweeter and much more down to earth. She seemed more like Vanessa, a regular guy wanting to explore his inner girl. Being a "bi-virgin," Vanessa wanted her first time to be relaxed, unstrained and special.
As she pulled into the motel parking lot, Vanessa knew her life was about to change irreversibly. A little afraid, but a LOT excited, she walked on trembling legs to the door of the room. Taking a big breath of air for courage, she knocked on the door.
A few seconds later it opened and a sweet vision of CD loveliness said, "Hi Vanessa", I'm Kimmy."
Vanessa stopped and took a good look at Kimmy. "She" was exactly what Vanessa was hoping for. A true crossdresser, not a "she-male" but an attractive guy looking feminine and sexy in women's clothing.
"I've soooo been looking forward to this," confessed Vanessa. "I'm nervous, but VERY excited."
"Me too," cooed Kimmy in a sultry soft voice. "But relax and let's enjoy this afternoon."
With that, Kim circled her arms around Vanessa's waist and pulled her in close. As Vanessa's face was drawn very near Kimmy's, she looked into her eyes and parted her lips in hopes of a kiss. Kim did not disappoint, as she met Vanessa's lips with a delicious welcoming kiss that made Vanessa tingle all over! Vanessa could feel Kimmy's hardness pressing against her and the kiss grew longer and more passionate. Feeling bolder, Vanessa felt under Kimmy's plaid mini-skirt and found a stiff cock encased in silky pantyhose!
"MMMmmmm...that feels nice," Vanessa whispered into Kim's delicate ear. And without another word, she knelt down onto her knees and lifted the front of the skirt. She found herself staring at a beautiful hard cock pushing out from inside the pantyhose crotch. There was pre-cum oozing through the fabric. Vanessa snaked out her tongue and tasted the creamy fluid. It was wonderful, she wanted more and began to wrap her lips around the sexy cockhead.
"Hang on lover," suggested Kimmy, "I want too see you as dolled up as me before we go much further." Vanessa was so into her first taste of savory prick that she'd forgotten to take time to "transform" for her new lover. With that, she looked up at Kimmy and took another long, slow slurp and stood up on wobbly legs. After a quick wet kiss to share Kimmy's sweet juice with her, Vanessa turned and went towards the bathroom.
Shaking with incredible excitement, Vanessa stripped in a matter of seconds out of her male clothes. In just a few short minutes, she had slipped into her sheer, black pantyhose. While almost finished with her make-up, there was a knock at the door.
"Vanessa, are you almost ready, I have to pee," pleaded Kim.
"Give me a couple more minutes," replied Vanessa, as she applied lip gloss over her sexy red lipstick. Satisfied with her "girl-face," Vanessa figured she looked good enough for Kim to see her even if she hadn't finished dressing. When she opened the door, Kimmy gasped at the transformation!
"MMmm, I like," she chimed.
"Thank You," smiled Vanessa, "I better let you do your business now"
"Actually...", said Kim, "Remember that one fantasy you listed on your web page?"
Vanessa smiled big, "You mean the golden shower one?"
"Yes," Kim smiled back, "You still wanna explore that?"
"I SURE do!" exclaimed a very aroused Vanessa. She then moved her bag of girlie stuff out of the bathroom and onto the bed. When she returned, Kim was standing on the toilet seat with her pantyhose pulled partially down and her skirt hiked up, holding a small camcorder.
"Ready Baby?" she inquired.
"Mmmm, yes, I can't wait!" answered Vanessa as she climbed into the bathtub. When she was positioned on her knees, she looked up at Kimmy with a pleased, hopeful look as she stuck out her tongue...awaiting.
Kimmy focused the camera on Vanessa's face just before the first few drops of piss landed on her nose and cheek. When the full stream started, she was able to guide the golden liquid better and targeted Vanessa's wide open mouth. In only a few seconds, it overflowed out of her mouth and down her chin. Kim then aimed the flow at Vanessa's closed eyes and all over her face. Vanessa was in heaven! The warm pungent piss filled her nostrils and some trickled down her throat...mmm, delicious! Then she felt her hair being soaked and felt the wet warmth running down her chest and nipples. As the shower subsided, Vanessa opened her eyes and looked into the camera lens and smiled. She raised up and took Kimmy's dripping cock in her hand and steered it towards her mouth. In a flash, Vanessa had the head in her eager mouth, licking off piss & pre-cum with her flickering tongue. Kim was in such shock and pleasure, she had difficulty keeping the camcorder focused on the hot action!
Vanessa was in her own little world. Finally in just a few moments, two of her ultimate fantasies had been fulfilled...being pissed on and sucking cock! She was like a woman possessed as she buried Kim's cock in her throat and bobbed back and forth onto it with increasing speed! Kim was also speeding...towards one of the most explosive orgasms she had ever experienced! As her cock got yet harder and her legs unsteady, Vanessa knew what was "cumming." She pulled her cock-hungry mouth off Kimmy's rock-hard tool and laid back against the wall in the tub.
Kim stepped down off the toilet and aimed her cock at Vanessa's piss covered chest and fired several globs of cum all over Vanessa's titties! After the mind-blowing orgasm, Vanessa stood up and Kimmy began licking her still warm cum from Vanessa's chest...stopping occasionally to deep kiss her lover. Vanessa was growing hard herself and moaned as Kimmy rubbed her cock through the wet pantyhose.
Vanessa spread her feet apart and nuzzled Kimmy's ear as she cooed, "Finger my pussy, Kim." With that request, Kim slid her hand down the back of Vanessa's pantyhose and felt around for the entrance to Vanessa's "man-pussy." When she pushed her middle finger in, Vanessa pushed back and Kimmy's finger slid in with ease as Vanessa gasped. Kim continued kissing Vanessa as Vanessa's ass began responding to the finger-fucking she was getting. Vanessa took Kimmy's other hand and placed in onto her hose covered cock. As she ground her ass onto Kim's finger, her cock rubbed Kim's talented hand. Vanessa stopped kissing Kimmy so she could stare into her lover's eyes and tell her how much she was enjoying herself.
"Oh god, Kimmy, finger fuck me...it feels SOOoooo good...I love it!" Vanessa cried as she shuddered in ecstasy in Kim's arms. "OH OH ohhhhhh, so good, so hot, mmmm, gonna cum soon!" Vanessa moaned loudly as her chin trembled. Kim felt Vanessa's cock begin to throb as she got a handful of warm cum through the crotch of the black pantyhose. Vanessa's body continued to jerk and spasm even after her cock stopped. She semi-collapsed into Kimmy's arms and sighed a very satisfied sigh.
"I think a nice shower is in order," offered Kimmy, "I'll soap your hard to reach parts if you'll do mine," she coyly said.
"Ok, Baby, anything you say", breathed an exhausted Vanessa.
"ANY thing?" replied Kim, with a VERY devilish twinkle in her eye...