It Happened on a Dare Pt. 03

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The journey continues.
1.4k words
4.55
8.9k
10

Part 3 of the 5 part series

Updated 06/16/2023
Created 03/11/2023
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dodgeboy2
dodgeboy2
447 Followers

Another few weeks have gone by living working hours as Jay but living the remainder of time as Janelle. Evenings dressing in sexy lingerie, shopping as a woman and even getting complete body laser treatments as a woman, surprised the technicians didn't seem surprised once they saw his cock when they treated him. After the treatments were done as he admired his naked body from his bedroom full length mirror if was then and there he decided to fully embrace his inner self and vowed he would one day soon live solely as Janelle telling himself he was born to always be a woman.

Finally the day had come when she was ready visit a club in hopes of meeting guys, his only concern was how and when they should be told of her secret. After taping her cock down tightly she slid her legs into a bright red pair of lacey panties loving the feeling as they rested against her trapped girly cock, she rubbed her hand up and down those panties surprised how invisible it felt down there making her feel even more of a woman. Next came a very shear pair of light reddish stockings held up by a matching red lace garter belt. After taping on her silicone breasts, a nice b-cup size pair that seemed so appropriate for her tiny body, on went the matching red lace bra. Standing up she admired herself in the mirror amazed how naturally shapely her small hips looked against her tight little butt, "hmm I look fucking hot," she said to herself. As she looked through her closet, which now was filled with 90% women's clothing, she decided on a deep red dress with a modest v-cut matching it with 6" red stilettos thinking the dress would accentuate both her breasts and thin waist while the heels would make her shapely legs appear longer.

After she was dressed and her makeup was done she went to her car becoming both excited and more hopeful as she noticed the looks she got on the stroll before opening the car door. She arrived at the club around 9:00, there was a long line filled mostly with men, maybe 30 men to 5 or 6 women, when one of the men who worked the line walked up to Janelle telling her to follow him as he let her inside.

Once inside the club appeared almost full the male to female ration seemingly at least 4-1 making her hopes for finding her 1st male lover to elevate even higher. Walking over to the bar with all the stools full six men jumped off offering theirs to her. The only woman at the bar she could feel so many eyes staring at her before a man walked over and stood near her.

"Hi I'm Kevin, may I buy you a drink?" he said.

As she turned her head she noticed a handsome man maybe 30ish with light brown short well cut hair, big brown eyes, close to 6 foot and very well built (not overly jacked or anything, just a sexy well fit look). Her breath almost seemed to be taken away for a second before she finally held out her hand very daintily before saying, "hello I'm Janelle, thank you I would love an espresso martini please."

After ordering her drink and a man leaving the bar Kevin sat down next to Janelle, as he sat he asked her, "so Janelle are you from around here?"

"Yes, I live in the city here and you are you from here?" she asked.

"I moved here a few months ago for work and I've just found the time to start exploring the night life." he said.

"So how do you like it? How does your girlfriend like it?" she asked, knowing he mustn't have one or at least she hoped he didn't.

"I like it a lot actually although I'm not really into the nightlife thing a lot and no girlfriend which is one of the reasons I moved to get away from a bad breakup. Actually a broken engagement to be honest, my best man was hooking up with her 3 months after we met and it continued until I found out about 6 days before the wedding when she told me she was pregnant with his child!" he said as a sadness showed in his eyes.

Janelle's hand reached out softly touching the man's cheek before saying, "I am so sorry that is a terrible thing, but you are so better off without her and I can't imagine she deserves you anyway."

The two talked finding they both had a love of sports and also tear jerking movies, they both laughed as they both admitted crying when an animal dies or a person loses someone close to them. One drink lead to another before Kevin asked her to dance.

As they danced Kevin pulled her in tightly her head leaning against his chest, Janelle could feel her heart pounding with so much excitement before he leaned in to whisper, "Janelle I would like to continue this if you would be open to it, may I ask if you would like to go out on a date with me?"

Janelle's heart seemed to flutter, she had hoped for just a hook-up but she really found she liked him and would love to know him better. Taking a short breath she exhaled before saying, "I would like that very much Kevin."

They danced to 4 more songs before retreating back to the bar talking before the bar closed, as they walked out together Kevin took her hand walking her to her car where they talked for a few more minutes as they leaned against the side of the car.

"God it's been so easy talking to you I hate to leave you, would you like to have dinner soon?" Kevin asked hoping she wanted the date to happen quickly.

"I'm free tomorrow, there is a nice French restaurant that opened recently if you want." she said.

"That would be great, how about an early dinner and then maybe we can take in the park and talk for a while more?" he asked.

"I would love that, maybe we can get to know one another a bit better." she answered.

A thought hit Janelle, "would he like me when he finds out and just when and how does she tell him?"

Janelle's thoughts were broken as Kevin asked, "Janelle may I kiss you goodnight?"

"Yes I would like that." Janelle said, her heart pounding waiting for her 1st kiss as a girl.

Kevin leaned in their lips met with a soft peck before he kissed her deeply for several seconds, Janelle's lips parted as Kevin's tongue slip in finding Janelle's own soft tongue. The two kissed passionately, tongues dancing together as Kevin's hands moved up and down Janelle's waist before Kevin's lips parted before Kevin said, "I think we both better leave before something happens and I want to get to know you so much better before that happens!"

Janelle's heart pounding and breath a bit labored finally said, "yes I think you are right, I don't want to be a rebound thing and it would be so easy to give in, goodnight see you tomorrow."

Kevin kissed her just on the lips before she entered her car and drove away, but not before she gave him her address.

As she arrived home after undressing and getting into her soft comfortable nightgown, as she lay in bed she was so excited but also so nervous again wondering just what to tell him and when should she. If she told him too soon would it end and also knowing it would be wrong not to tell him before it got serious.

Finally after tossing and turning she drifted off to sleep she dreamt being a girl making love to Kevin, as her legs spread there a vagina where her cock once was, as his cock enters inside her she could feel the fullness it fills her with. Awaking in a hot sweat just as his cock explodes inside her she said to herself, "I have to tell him tomorrow, but how?"

The morning came so quickly as she ate breakfast she tried to put together a speech of what to tell him but no matter how hard she tried she could come up with nothing that seemed to work.

"Oh well, I guess I'll have to just find a way to fit it in." she said to herself before turning on the tv...

dodgeboy2
dodgeboy2
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rainlilyseedrainlilyseed8 months ago

I think you are taking this short story thing to its limit. The 1st 3 stories should all be combined for one story, I' going to assume the next 2 instalments should also be included.

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