Alan and Stevie

Story Info
Alan falls in love with a transgender.
1.5k words
4.21
9.2k
3
2
Story does not have any tags
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My transition really began before I started first grade. Born a fraternal twin with my sister Joann, I envied her for the pretty dresses, her dollhouse and her toys. I fit in with Jo and her friends. She didn't put up a fuss when I got dressed in her clothes. My parents, on the other hand, were not okay with that.

Anyway that's water under the bridge. Now 23, I've been taking Estrogen since the onset puberty and Testosterone blockers since I turned 11. On the diagnosis of a child psychologist, my parents gave my transition their blessing.

A Saturday morning in May sees Jo and me at Spy Pond Park watching a flock of ducks. Some are poking their beaks into the rough grass where they might find a tasty morsel. Others are just walking about as if exploring. Children are playing nearby.

The day is more than just a nature walk. Important questions need to be asked and answered.

"Stephanie have you told him?"

My sister refers to Alan Benson, a dude whom I had met recently at work.

Alan is a cute blond with blue eyes. He is tall and lean.

He's a personable type, at least that's my impression. As far as I know he's single, at least he hasn't mentioned a girlfriend.

The fact that I never revealed to him is that I still have my penis. It's 5 plus inches long when fully erect. Not only do I still have it, but there are no plans to undergo SRS. Adam's Apple reduction and facial reconstruction are enough for this girl.

Otherwise my body has developed pretty much along the lines as that of Joann. There is something to be said for genes.

My breasts are a C cup. When I saw them just beginning to develop I could not have been happier. Nothing short of a terminal illness could have ruined the mood. Glimpes of Jo and my mom gave a clue as to what I would some day have.

"I don't know if he's gay or bi. It's not like I can ask him."

"No you can't," said Jo.

"He may be straight. I don't even want to think that but it's in the back of my mind."

In my effort to look sexy, I chose to wear a Grape lace- detail sleeveless top with ruffle hem, jeans and wedge-heal sandals. I painted my fingernails and toenails matte red. My full lips are coral-pink.

"So where are you guys going tonight?"

"He's meeting me at Za on Mass ave."

"That's a good place. My "x" used to bring me there."

My sister's "x" girlfriend is Katie Thornton, a petite strawberry-blond with green eyes. The two girls dated for a year before Katie ran off to join the navy.

I found Alan sitting at a window seat.

"You're looking good tonight."

There's a pickup line if ever I heard one.

"You're handsome as well."

We made small talk over pizza washed down with beer. Much of what we said had already been said but so what. Alan told a few anecdotes about his youth and friends from his youth.

"No girlfriends," I asked.

"Briefly in high school," he replied.

"What was her name?"

"Jane," he replied. "What about you, any X boyfriends?"

"No," I replied.

"Let's go sit by the pond."

How romantic.

"Sure," I said happily.

Tonight can make or break the relationship. I don't want him walking away just because of what's between my legs. I'm still a girl regardless of what anyone thinks. Maybe I'll hold off before I let him into my panties.

The temperature was still warm after 6 o'clock. We kept a leisurely pace on the paved trail. Chit chat amounted to little more than observations about the pond and the town of Arlington. We were barely aware of the passage of time.

"Stevie how was your date?"

"It went well."

"You're home early."

Joann knew that I did not get laid. I had come home far too early for that.

I plopped into the rocker near the sofa. She took a seat on the sofa. The Samsung mounted over the hearth was tuned to UPN 38 showing a movie.

By 9 30, give or take minutes, I yawn. Before 10 I yawn again and again due partially to boredom with the movie but mainly due to lack of sleep Friday night.

I retire to the bedroom but Alan is too much on my mind. My clothes come off and I stretch out naked on top of the bed covers. Lustful thoughts send blood rushing south giving me an erection. I want Alan fucking me.

Determined to ejaculate, I close my right hand around the shaft and pump it rapidly. My left hand slides upward on my breast brushing the nipple. A few minutes pass then thick white cum squirts a few inches.

A few days pass rather uneventfully. Alan and I spent very little time together outside the hospital, although we did talk on the phone after work.

Saturday finds me at work in MRI. Like any other weekend, my department is only half staffed. Very few patients are coming for tests. Alan works in Radiology taking x-rays but is off today.

During my lunch break I place a call.

"What are you doing today?"

"I played basketball this morning. Are you on your lunch break?"

"It's Very slow today. I saw just 3 patients so far."

"Let's hang out tonight."

"Sure," I replied.

We kept the conversation going until the end of my lunch break.

I guess this is as good time as any to tell him my secret. He hasn't seen "the family jewels" yet but at least I'll know whether or not to show those.

Back at our apartment Jo and I took seats on the third-floor balcony overlooking the spacious parking lot, walkways through the lawn and planted trees.

"It's time I tell him what's down there. Maybe the man parts will frighten him off but I'll deal with that."

"Good call," said Jo. She added, "better to tell him before showing him."

"I should probably do this with home court advantage."

"Another good call," said my sister.

Not long after that chat with Jo, Alan texted me from the parking lot. I hurried down to the front door. As we walked at a leisurely pace to his Honda I heard the words in my head.

We had walked about 50 steps in silence.

"I'm a transgirl."

"I don't care about that."

There was silence again until we came to a tiny patch of sand just outside woodlands around upper Mystic Lake.

I stood face to face with him. His eyes went to my crotch.

Seconds later jeans, panties and gaff came down letting him see for the first time my man parts.

"OH my god Stephanie," he exclaimed. "I said I didn't care. It doesn't mean that I want to have sex with you."

I asked, "not even if I'm post op."

He didn't reply so I let it go.

"I like you a lot."

I replied, "and I like you a lot."

I really want to have sex with you. Nobody has to know that you had a chick with a dick. I'll never tell.

"For what it's worth, I think you're very attractive."

My lips stretched into a smile. I'll work on him.

Somehow I knew it was a mere question of time before he would give in to his urges. It may have been his eyes going back to my dick that gave me the first clue.

Beside the water I let him pull me into a deep kiss. His hand crept to my ass then around to my manhood.

"We need to head for the bedroom."

"Mine or yours," I asked.

"Your choice," he quipped.

Night fell over the city. I closed my bedroom door softly behind us and pulled my shirt off slowly. I unfastened the lace strapless bra letting it slip to my feet.

"Nice boobs," he quipped then cupped them.

I pulled him into a deep kiss.

He eased me down to the bed and slowly pulled my jeans, panties, then my gaff all the way off. His thick hard pecs squash my soft boobs under him. His throbbing erect dick brushes mine. His kisses dive me crazy with desire. I ache for his dick to penetrate me.

Hidden in the nightstand draw are lube and a buttplug I use to pleasure myself.

"Nightstand on the left," I said softly.

I waited for him to go there then added, "top draw."

I leaned over my bed propping myself on my extended arms. Having filled me with lube, my lover rocked gently thrusting his thick cock tapping my prostate. I grunt softly masking my intense pleasure.

"It feels so good."

He reaches around me to my erect cock. His hand slides back and forth pulling skin with it bringing me to the brink of an ejaculation.

The sun brightens the bedroom before our eyes open. My boyfriend leans over to kiss my cheek and push the blanket off my naked body.

"Morning wood," I quipped making him grin.

"If you never have SRS I'm okay with your decision."

We went into the shower together.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
ShortyMacShortyMacalmost 2 years ago

Not a bad story. Would have been better with a bit more details about the sex.

Share this Story

Similar Stories

Burly Cowboy Meets Showgirl Clean meets someone Special.in Transgender & Crossdressers
Lizzie A small town girl with a BIG secret.in Transgender & Crossdressers
A Night to Remember A hermaphrodite learns to accept who she is.in Transgender & Crossdressers
Biking Buds When Doug crashes his bicycle he needs a caretaker.in Transgender & Crossdressers
Boys Go on a Bikini Boat Ride Six guys go on a boat ride for some discreet bikini fun.in Transgender & Crossdressers
More Stories