tagTranssexuals & CrossdressersInfluential Factors! Ch. 03

Influential Factors! Ch. 03


I awoke around 10am in the morning and fully clothed minus my shoes. I had to remove my make-up and take a shower before heading downstairs.

I tried to remember last night but had only faint memories.

I remembered hitting the bar, having a daiquiri, a double shot of something, and some guy wanting to dance with me. I remember we danced and drank... a lot of both; and I if I recall I think we kissed.

After removing my makeup I went to the bathroom and rinsed well with mouth wash just in case I actually kissed him...gross.

I immediately turned on the shower and jumped in; it was a bit cold but woke me. I tried to remember last night while the sensation of the water ran down my body. Once done I dried off quickly, brushed my pearly whites, used mouth was again, brushed my hair, and reentered my room.

I just remembered I had no clothes and had only female attire so I looked for something comfortable to wear. Then I noticed my wife laid out clothes for me for today while I was in the shower and another note that read 'Read the list of things not to do today, get dressed, and come downstairs'."

She laid out an olive colored cold shoulder dress which had kimono sleeves and looked to be mid thigh when I held it up to me. A pair of tan open toed slide sandals with upper leather straps with a two and a half inch heel and a cork wrapped block heel. Again, I accessorized with gold jewelry. I brushed out my hair one last time; though I thought it looked great the first time, and then I applied light make-up.

I smelled fresh brewed coffee and quickly made my way downstairs

"Good morning," I said.

"Good morning," she replied.

"What's up with the 'not to do list' you left me?"

"You have surgery tomorrow," she told me.


"No, I know what you're going to say,"

"It can't wait a couple of weeks?" I begged.

"That wasn't the deal April," she said keeping her cool.

"I know...but I'm a little nervous," I said hesitantly.

"We've all ready discussed this..."

"I mean last night,"

"What about last night?"

"Did I kiss a guy last night?"

"Passionately," she smiled.

"Fuck!" I couldn't believe it.

"You would have if I didn't intervene," she giggled.

"I was drunk...he got me drunk," I quickly made an excuse.

"Are you sure it was the alcohol?" she giggled again like she was thoroughly enjoying seeing me squirm.

"Yes, like I stated before, I'm just a cross-dresser and have no intention of getting fucked by some guy,"

"And like we discussed before, you sure liked it up the ass, and you certainly loved swapping spit with Mike last night,"

"Mike, shit, that's who I kissed...I mean kissed me,"

"I believe it was totally mutual," she smiled.

"Really, if my memory serves me right I believe you kissed someone last night too, now that I think about it?"

"Listen, according to you your cross-dressing has only been for self enjoyment and nothing else right?" she asked sincerely.

"Right," I replied.

"I have never fooled around on you either but I admit I let him kiss me in hopes you would let Mike kiss you,"


"Because I needed to know if you would kiss a man and you did,"

"But I was drinking...and he kissed me...and you were kissing some guy..."

"And instead of getting jealous you kissed him,"


"April, how far will you go without a single push from me?"

Right then my cell phone rang.

"Fuck, it's Mike,"

"Mike from last night?"

"How do I know,"

"Are you going to answer it?"

It stopped ringing after the third ring.

"I think..." I began as my text lit up.

Text: "April, I really enjoyed last night and would really like to see you again. How about a late afternoon lunch?" I read Mike's text out loud.

"Sounds like a great guy," Jill remarked.

"What do you mean by that?" I asked curiously.

"Just that he's a nice guy," she answered.

"But I'm not into guys,"



"It sounds innocent enough, it's not like you have anything planned for the day anyway so why don't you go out to lunch with him,"

"I don't know,"

"It'll give you a reason to dress up,"

"I was hoping to do something with you today," I told her

"Sorry, Niki and I have girl plans,"

"Like what?"

"Brunch with some of the girls, the beach for a hour or so, and then shopping,"


"April, you'll get to experience of dating from a woman's point of view,"

"I don't know," I was hesitant.

"It's an innocent date; I promise I won't hold it against you. Besides, you have this whole female persona perfected, go for the experience," she stated.

"And last night...?"

"Fine, you go out with Mike and I'll forget about everything thus far except the contract," she said.

"It's a deal," I said enthusiastically. Deep down I really wanted to experience a date as a woman, well, from the other side of the table. I'm a curious cross-dresser and that's all, I have no desire to be fucked or orally satisfy a man; but since last night would be forgotten I jumped at the opportunity.

Text to Mike: When can you pick me up?

Mike's text: Is around one okay with you?

Text to Mike: Perfect

Mike's text: Address

Text to Mike: (( address))

Mike's text: See you soon

"Well, is it on?" she asked me.

"Yes, he's picking me up around one or so," I replied.

"Don't blow it!" she remarked.

"What do you mean don't blow it; are you being sexual or what?" I asked.

"No, I'm just saying you might want to see him again, that's all," she laughed.

"I told you...I'm just a cross-dresser,"

"Actions speak louder than words," she laughed.

"Oh, you're so annoying,"

"And you're so beautiful when you're annoyed," she laughed as I joined her.

I fully understand her hesitation from letting me off the hook. If she started wearing men's suits and got a crew cut I'd be a little nervous she was into women and I would relate it to the "no sex" attitude because she was getting her fill somewhere else.

Nonetheless, I was extremely excited about my date with Mike and wanted to impress him so he would really be into me...for the experience of course.

"I think I'll get ready," I told her.

"What's wrong with what you're wearing?"

"It's um...you know..."

"Not sexy enough!" she remarked.

"It's all about the experience...and showing you I can dress sexy without being into men,"

"Now you're showing some initiative," she said.

"I just want to look pretty for my date, I mean, its part of my cross-dressing...to impersonate... to come off as a women that is," I explained.

I quickly pranced in my heels to the steps, slipped out of my shoes, and made my way upstairs. There, I changed my dress to a white swing dress with rounded neckline and short sleeves with lattice cut out detail. Not only was it cute and sexy it hid the fact that I had no breasts. Once I slipped it on I grabbed a pair of natural ankle strapped wedges, because I love wedges, and a matching dainty purse. I did my nails first in ruby red and waited for them to dry. Then I took my time with my makeup until I was completely satisfied using ruby red lipstick to match my nails and completed myself with one of Jill's perfumes from the master bedroom that I love so much. Then I headed back downstairs to wait for Mike.

"Mike must have made a real impression on you,"


"You're extremely hot and you smell expensive; you're trying to impress him I see,"


"You had to go in to my room to get it,"

"Whatever," she had me again; I did actually want to smell nice for him.

Did I subconsciously try to impress Mike for any other reason beside the experience?

Did I really fall for him last night?

I don't know the answers myself...

I can't think straight...

Don't do this to yourself; you're only a cross-dresser...

"Ding-Dong" the door bell sounded bringing me out of my trance.

I hurried to the door with Jill in tow.

"For not wanting to go you sure are in a hurry," Jill told me.

"It's the experience,"

"Maybe more,"

"I just don't want to keep him waiting; it's rude,"


"Your rules...my manners," I said smiling.

When I opened the door I remembered most of last night. Mike was tall and handsome; I was as happy as a girl on prom night.

"Hey Mike." I greeted him with all smiles.

"April," he said kissing me on the cheek.

"You two have fun," Jill remarked.

"Thanks Jill," Mike replied to her as he took my hand and walked me towards the car.

I smiled in glee as I peered back to see if Jill was watching us; she was. Mike opened the car door for me; I saw Jill smile and wave to me as I looked at her out the passenger side window; we were both smiling as she shut the door.

I admit, getting ready takes some time but having a nice looking guy pick you up, kiss you at the door, and open the car door for you is so romantic it gives me goose bumps; and admit, though rarely, I have wondered about how a girl felt at this moment but never thought the girl; it was surreal. I fell for it and enjoyed the rush of the moment almost forgetting that I wasn't a girl.

Mike and I gabbed like two lovers that haven't seen one another in a year. We finally arrived at our destination, the waitress walked us to our table where he pulled out the chair for me as I sat; what a gentleman. He had me where he wanted me and I wasn't to sure that I wanted what he was giving.

"Can I get you something to drink?" the waitress asked.

"Just water with lemon slices," I answered.

"I'll have a beer, whatever's on tap," he replied.

"We have Bud and Coors neither are light," she told him.

"Make it a Bud,"

"I'll be right back," she said cheerfully.

"So tell me about yourself," Mike asked me.

"Not a lot to tell,"

"Come on, I'm sure there's something you can tell me,"

"Well, I'm from the east coast. I have a master degree in music and business and just got a job with my cousin's husband to run a chain of stores,"

"Is that what brings you to California?"

"You mean besides the beautiful beaches and weather?" I giggled.

"You have a beautiful smile," he told me.

"Thank you," I smiled than sighed.

"Did I say something wrong?'

"No, a girl always loves a compliment,"

"Then what's wrong?"

"My mom fell down the steps last night..."

"Sorry to hear that; is she okay?" he asked sincerely.

"She'll be fine..."

"That's good to hear,"

"Mike you're really a nice guy and everything but..."

"Uh oh, I think I just hit the friend status,"

"No, it's nothing like that," I told him.

"Then what is it?"

"I'm going back home for at least six weeks to take care of my mom..."

"I understand, maybe we can get together when you get back,"

"That would be great," I smiled.

Why did I do that...?

I should have said adios amigo...

This was my chance to walk away...

What the fuck was I thinking?

I was thinking I want to be his girl...

But why...how...?

I was flattered with his desire to be with me which made me a bit...excited; then again there was that deal I made with my wife that I had to give dating a chance to prove I wasn't gay which in itself is contradictory. Though however strange it may sound I get to experience being a woman from this side of the table...and I'm truly enjoying it.

My passiveness and flirtatious behavior with Mike was confusing to me; but for some reason I was drawn to him. I wanted his attention; but why?

"I'll give you a call in six weeks and we'll go from there," he offered.

"Sure, that works for me,"

I kept sucking him in instead of spitting him out.

The waitress arrived with our drinks and we both ordered a burger with the works, fries, and coleslaw; thanks for my fast metabolism I could freely eat what I wanted to!

We talked for a while, then the food arrived, and then we talked some more as we ate.

He was charming and charismatic...sometimes I thought I was a real girl on a real date. I basically just lost myself in the moment and I laughed and giggled as he amused me with his flirting and his wit.

I was basically in heaven!

He eventually got around to asking me out to a club later which I gladly accepted without hesitancy; never remembering I was in fact a male until after the fact.

Was it because I really liked Mike?

First he took me to the beach for a walk along the boardwalk to pass time. There we talked, stopped at the stores to look around, and then went to Kone On 'Da Beach for some ice cream.

We sat on a bench overlooking the ocean where he got friendly with me. He put his arm around my shoulders and kissed me. I gave in to my emotions as I allowed him in and to passionately kiss me.

My thoughts were teetering back and forth; I had no clue to who I was, what I wanted, or what I was doing here.

Finally, we headed to the club, once inside he introduced me to his friends. After introductions, Bill, one of his friends asked me if I wanted a drink.

"No, I'm okay,"

"This rounds on me,"

"No thanks,"

"Last call, you came all this way to have a good time," he smiled while a few looked on.

"Fine," I laughed.

He called a girl over and ordered drinks but when she brought us our drinks I was shocked. All the glasses were filled with ten ounces of Goldschläger.

Goldschläger, the girls called it, they do this sort of thing every now and then; can you handle it?" Bill asked.

"No," I smiled though it must have been twelve ounces in one glass.

"You don't have to drink it if you don't want to," Mike whispered in my ear.

"I'm okay," I smiled though I wasn't supposed to drink but I felt uncomfortable not joining in.

"Cheers," they all screamed as we all chugged down our Goldschlägers.

The girls were on a tear tonight as they took to the dance floor dragging me with them. The Goldschläger wasted no time in finding its way upward clouding my brain cells with any rational thought. The nine of us danced as the boys joined in the next song one by one. Each girl waved bye to the remainder as their date, boyfriend, or husband pulled them from our group. I waved to Angela and Mary Joe as Mike pulled me away from them.

My head kept spinning as I clung to Mike; his hands rode down my back finally settling on my ass where he wasted no time to cop a feel.

I giggled as our bodies ground together and his hardened member poked at me through his pants.

He kissed me and he pulled away.

Jill and I haven't had sex in ages, his kiss left me hungry for attention, I peered into his eyes and that's all he needed to kiss me again.

His tongue passed through my all ready parted lips and met mine; our tongues danced raising a new level of excitement I haven't felt since the last time I made love to Jill.

"Mmm," I muttered as my breathing got heavier and heavier as I melted in to each kiss; April was alive!

The next thing I know I was home in the family room making out with Mike.

My hand accidentally falls to his crotch and I can feel his swollen member. I start to pull it away and Mike pulls my hand back to his crotch... laying the palm of my hand on his cock.

"Please April," he begs.

I don't remember much but I must have teased him into a frenzy or he wouldn't be begging me for relief.

"Please relieve me...nothing more, I promise," he tells me releasing me from our kiss for a second.

My head was still spinning; I felt the urge to please him as I rubbed his cock through his pants.

"Thank you," he tells me releasing me from our kiss and continuing again.

Obviously he was getting excited as I continued rubbing him but it wasn't enough as he broke the kiss, unbuckled his belt, undid his button and zipper, raised his butt, and pulled down his pants.

"Sorry," he apologized as he kissed me again taking my hand and wrapping it around his huge cock.

I began to stroke him as we kissed eventually peeking down at his huge hardened member.

He broke the kiss and leaned back into the couch as I laid my head upon his chest to stroke his cock better and get a better look.

"Oh gawd April, you're amazing,"

My head was still spinning and my eyes were now locked onto his shaft.

"Ah," he continued as time passed.

My eyes were fixated on his shaft as I continued to pump away. Then precum, the head of his cock glistened, and now my eyes were mesmerized by his manhood.

"Oh yeah," he muttered.

"What pushed me to spread his legs and kneel between them I couldn't tell you...but I did. His glistening knob mesmerized me and I wanted to taste him. I licked the precum from the tip of his cock and was amazed how much it tasted like Goldschläger!

"Thank you April," Mike muttered.

It was just a sound in the background as my lips cupped the dome of his cock and my tongued teased it. After some time I stroked his rod as my lips rode up and down his shaft.

"Oh gawd," he repeated over and over as I molested his cock with my weapon of choice.

Time passed... my head not much clearer; I came to the conclusion I had his cock in my mouth and was fully enjoying the sensation of my actions.

"April... you don't... oh gawd..." he muttered.

This whole night was so dreamlike!


I couldn't stop now; not now!


I wanted him to cum in my mouth, I wanted to taste him, swallow him, and to enjoy him; I wasn't going to stop!


This was my moment, no matter how passive the female being may be, April was in control, and she had all ready made up her mind it would be her way and no one else's.


His cock twitched as he released himself inside my wanting mouth.

"Oh gawd April..."

The realization of me down on my knees and sucking my first cock shocked me partially back to reality as his jizz hit the back of my throat. Though my head was still spinning from a night of drinking I knew I had to swallow every last drop otherwise it would leave a tell tale sign somewhere on the couch. I did what I could and licked his cock until he was all clean and then turned to the back of my hand for the remainder.

"Thank you that was the best blow job I've ever experienced," he admitted.

"Thanks, pull your pants up and let's go upstairs," I giggled.

"Really!" he said excitedly.

"To sleep, I can't let you drive home wasted,"

"I'm okay," he said pulling up his pants.

"Are you sure?"

"Yes," he pecked me on the lips as I walked, more like staggered, towards the door.



"If you tell anyone, I mean anyone about tonight, it's over between us,"

"I won't,"

"I'm serious, not even your closest friend,"

"It's all good, I don't tell bedroom secrets, I'm not like that,"

"Okay, call me,"

"Bye," he said after a few passionate kisses.

Mike was happy and I was ecstatic after my first blow job!

Still wasted I half crawled upstairs, slipped out of my shoes, and fell back on my bed where I instantly fell asleep.

Report Story

bygummidurango60© 2 comments/ 9069 views/ 11 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartUltimak, hawken333 and 9 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Santacruzman07/29/17

A little late reading this

Well, the first step is taken. He's no long just a straight guy that likes to wear dresses, he's fallen into being bi and by the looks of it, enjoying it. I think that Jill is right about him and ismore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by 300bowler30007/06/17



If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 2 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission.

Post comment as (click to select):

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: