tagTranssexuals & CrossdressersRealization vs. Reality

Realization vs. Reality

byThrockmorton©

This story is one hundred percent true to the best of my recollection. I wanted to tell someone for so long, but never have, until now. Feed back is appreciated, and applications are being accepted. Read the story, you’ll understand.

To get to the story…


So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a first string heterosexual male. From my earliest memories of when I began to notice girls, I have always delighted in the wonders of women. I became sexually active at age 16, and there has never been any question in my mind that the only sex that aroused me sexually was of the female persuasion.

That being said, when I was 12 years old, I had and experience that changed me forever. I had a friend, Tommy, who was 14. He was bigger and stronger than me, but we got along well. One day, while wrestling, he pulled my shorts down. I struggled, but he was too big and strong, and he held me down and played with my pubescent package. He kept telling me to be quiet and relax.

After playing with my crank like it was some kind of toy, he turned around so that he was sitting on my chest facing me. He had pulled his schlong out his button fly’s, and was jacking his dick right in front of my face. I was flabbergasted, but I couldn’t look away. When I did look up into his eyes, he was smiling. He lifted his butt off of me and put the engorged head of his leaking cock to my lips.

“Suck it, or I’ll tell everyone that you’re a fag” he commanded. I don’t know why, but I didn’t hesitate. I was not attracted to other boys, but this hard cock in my face was making me horny. I remember distinctly the strong pungent odor of his cock and feeling of the hard, yet soft flesh in my mouth.

Just before he came, he pulled his dick from my mouth and shot his load on my chest. I remember something like a mix of relief and disappointment that he hadn’t finished while I was sucking on him.

That was my one and only “gay” experience. I have never since been attracted to men, and I have reveled in the physical relationships I have had with a variety of woman over the last 24 years.

So, here I sit, 40 years old and just now realizing that while I am not attracted to men, I love cocks. I love mine, and I love looking at others. Hard or flaccid, black, white, or brown. The thought of a hard cock makes my dick twitch. I guess I have always felt this way, but I guess I never really got it because the men attached to the cocks I have seen inspire no sexual feelings at all.

It was the damned internet. Shemale porn everywhere. And while the majority of the images inspire no lascivious thoughts in me, I cannot help myself from seeking them out. And every once in a while I am rewarded by the image of a gorgeous woman with great tits, fine ass, and a big hard cock.

So I fantasize, and jack my dick to thoughts of one of these gorgeous lady/boys dominating me and making me suck her cock. I have even bought dildos and fucked myself in my virgin ass to thoughts of being taken by a beautiful shemale.

I have at times thought to act on my obsession, but porn, the occasional 1-900 number, and chat rooms are as far as I was able to take it.

That is until I met Jamie.

Okay, about me. I am 6’3” tall and weigh about 250lbs. Because of my height, I carry the weight well. I am not ripped, but neither am I a slob. I work in construction, and am in pretty good shape considering my eating habits. I am average looking. The kind of guy some women think is handsome, and some wouldn’t spit on if my head was on fire. As far as my “manhood”. I guess it is right for my size. I don’t know how long it is exactly, but I have never been embarrassed to take my clothes off in front of others. And if what I have seen in locker rooms is any indication, I’m pretty well off.

My job takes me out of town a lot, hence the poor eating habits. But the travel affords me the opportunity to experience a lot that I would never have the opportunity to otherwise. I am divorced, with no children, so I am not really tied to anyone or anything, so I am able to “play” when I am out of town.

I have gotten the art of seducing younger women down to a science almost. And I have enjoyed the company of more than a few during my travels. Sex isn’t always, or even usually the result of these indulgences, but it happens often enough to keep me happy.


Now the story.

I was working in New York. About an hour away from Manhattan. I was going to be there for about four months. Being that close to the city, I had the opportunity to go there on the weekends once or twice. I considered going to a club where I might actually meet a real shemale, or even hiring a tranny escort, just to have the experience. But I chickened out each time. I had fun in New York though, even got laid once.

So I’m working in this little town and spending my weekends playing golf, or going to the movies. I wasn’t planning on going back into the city anymore, so my dreams of finding me a real shemale slowly faded.

One night, about two weeks from the end of the job, I decided to go out to a bar down the street. It was within walking distance, and I had kept telling myself I would check it out before I went home for good.

The food was good, the beer was cold, and they had live entertainment after 10. It was just before midnight, and I was finishing my fifth and what I swore would be my last beer. As I was turning to leave, this young woman sat down beside me.

I guessed her to be about 25 or so, with long blonde hair and a really nice figure. She was about 5’8”, tall for a woman, and slim, with what appeared to be a nice full set of tits. She had a thin waist and her hips flared in a way that made me do a double take. She was wearing a tight multi colored dress, cut low in front and with a hem line that was threatening to climb above her thighs as she slid onto the stool next to me.

I sat back down and turned towards her.

“Can I buy you a drink?” I asked. An oldie but a consistently successful ice breaker.

“Sure she said, if you sit and have one with me”

Now there was no way I was walking out with that kind of invitation handed to me by this hot little number.

I sat back down and she ordered for both of us.

“Two shots and two drafts barkeep” she said, smiling mischievously.

The bartender didn’t ask shots of what, or what kind of beer, so I figured her for a regular.

“I’m Jamie” she said, holding out her hand.

“Hi, my name is Tim” I reply, taking her hand. It was warm and delicate, with long tapering fingers and well manicured nails.

The shots,(whiskey), and the beers( draft lager), arrived and we moved to a table.

We chatted for awhile about nothing in particular. The band was playing and announced they were going to “slow it down” a little.

Jamie asked me to dance, and being semi inebriated and increasingly horny, I agreed. The thought of this lovely young woman in my arms was arousing carnal thoughts in me.

She fit perfectly in my arms, and as we swayed to the music, she whispered in my ear, “wanna get out of here?”

I leaned back and just grinned at her. Her green eyes sparkled with delight as she took my hand and led me off the dance floor and towards the door.

We both made a detour to the bathrooms, and then were outside.

“Where do you want to go?” I asked.

“Where are you staying?” Jamie responded.

“I am staying at the Hampton Inn just down there” I told her, pointing vaguely in the direction of my hotel.

“Sounds good to me”

We walked hand in hand down the brightly lit block. Just before getting to the hotel, we passed a liquor store where Jamie insisted we pick up a bottle of wine.

We got back to my room, and I realized that I had no wine glasses, and no corkscrew. I got two hotel glasses that were clean, and I opened the wine with my pocket knife.

We were both giggling and laughing at the situation.

After a couple glasses of wine, and more small talk. Jamie looked into my eyes and said, “are you going to kiss me?, or what?”

I broke out laughing, it was just funny for some reason.

Jamie joined in and somehow during the laughter, I wound up closer to her. Her beautiful almond shaped eyes looked into mine as I leaned in for a kiss.

Her full and sensuous lips found mine. They were so soft and wet I almost came in my pants.

I have always liked kissing, and we spent a long time doing just that. Kissing like lovers who have known each other for a long time. There was some touching and caressing, all over the clothes though.

Sometime during this necking marathon, Jamie’s hand ended up on my thigh. High up and close to my straining cock.

While we kissed, she let her hand slide up and over the outline of my cock, caressing it through my khakis.

I began to fondle her full breasts through her dress, and eventually was able to maneuver her so that I could slide her dress off her shoulders and expose two of the most beautiful tits I have ever seen. The were so round and firm. But soft at the same time. Her areola’s where dark brown and large with nipples that were hard and long, just the way I like them.

I tried to get her to let me slide the dress under her hips so I could see the rest of her body, but she had other plans.

“Just lay back cowboy, its time to play” she said grinning like the Cheshire cat.

Lay back I did, and she leaned over me, planting first one nipple, and then the other in my mouth. She left each there for only a few seconds, then repeated this. The second time, I heard her began to purr, yes purr.

Then she said “Bite Them!!”

“what?”

“BITE THEM GODDAMMIT!!!, BITE MY NIPPLES, HARD!!!!”

So I did.

She began to squirm and moan like no woman had ever done with me before. Jamie reached behind herself and grabbed my cock in a vise like grip.

“If you want me to take care of this, you better bite me harder.”

I wanted her to take care of my cock in the worst way, so I applied yet more pressure with my teeth.

“Yes, yes, yes YES!!” she screamed. And I swear I think she orgasmed right then.

My nipples are sensitive, so I could relate, but I had never shot my wad just from nipple play. WOW

As soon as her breathing began to come back to normal, she slid back off my lap and knelt between my legs.

Jamie undid my belt and unzipped my fly, then began sliding my pants down. I raised my hips to facilitate this action and as my pants were fairly ripped off my legs, my swollen cock sprang to attention and waved in the air merely inches from this sexy woman’s panting mouth.

“AHH” she said, more of a yell than a whisper.

She opened her mouth and swallowed my cock in what seemed like one motion. I shave my nether regions and she was licking my shorn balls and taking them in her mouth in a way that was making me vibrate.

Then she moved back to my rod. Licking and slathering it with her tongue. She held the base of the shaft with one hand, and my balls with the other.

As she began to slide my trembling member over her tongue and down her throat, she started squeezing my nuts with every down stroke.

I never would have believed something that hurt like that could feel so good. Damn, I was in heaven.

As I began to feel my impending orgasm build inside me, I was torn between letting her take me over the edge, and wanting to take her clothes the rest of the way off and fuck her good and hard.

As this decision was being weighed in my fevered brain, Jamie took the reins and relieved me of the responsibility of making the choice.

She pulled back, my incredibly swollen cock bobbing just in front of her beautiful face.

“You like?”

“Oh god YES”

“You want more?”

“Yes yes yesss”

“You want to cum in my mouth don’t you?” she asked quietly.

“Yes, but I want to treat you right too Jamie, I do. Please take off your dress and let me taste you” I pleaded.

“Are you sure that’s what you want?”

“YES”

“Are you positive?”

“YES, YES, YES”

“Okay, but remember, you wanted it”

All I could think of was how badly I wanted to see this seductress naked. How I wanted to run my tongue all over her body and taste every inch of her skin.

Jamie stood, and for the first time all night looked unsure of herself.

She turned her back to me and slid her skirt down over her hips, hooking her thumbs in her G string and taking that down as well.

She stood with her legs together as she bent over to disrobe, and in the limited light, I couldn’t see her pussy, but her ass was incredible.

I have always been an ass man, and her’s was first rate.

Slowly she began to turn towards me. As she turned completely around to face me I looked at her eyes, then her lips, her shoulders, her beautiful big breasts, her narrow waist, her flaring hips, her big, hard cock…

Big hard cock?

I did a classic double take, then realized that all my dreams and fantasies were standing right in front of me.

The worried look on Jamie’s face disappeared as she saw the smile on mine.

She stepped to me and said, “still wanna taste me?”

In response, I grabbed her hips and pulled her to me. With her standing, that beautiful cock was right at face level. It was about the same size as mine, but not as fat. I smelled the glorious odor of her cock and balls. I stuck out my tongue and began to taste her.

Jamie shaved completely like I did, and I spent a long time teasing and tasting her.

Finally, I opened my mouth and slid down over her beautiful dick.

Within minutes she was pumping my face like it was her job. I squeezed her balls as she had mine, and she began to shake and moan like she did when I bit her nipples.

I had never tasted cum from another cock before, but I was ready to do it now! I wanted her to come in my mouth, down my throat. I needed it.

Once again, Jamie had other ideas. She began to talk to me again. Her voice rough and stern like when he told me to bite her harder.

“Oh, you are a good little cock sucker aren’t you?” she commanded.

“MMMMM_HMMM” I moaned around her cock as she continued to fuck my face.

“You want to taste my cum don’t you?” she asked.

Again “MMMM_HMMMM” was all I could manage.

“Well you will bitch, but not yet!” Something in her voice scared and excited me like I had not thought possible.

She pulled her cock from my lips and I actually whimpered. I wanted to suck her so badly.

She turned and grabbed her purse. She rummaged inside and came out with a tube of lubricant.

Now as I said, I am an ass man, and I enjoy anal sex, but all I wanted was her cock in my mouth at that moment.

I began to tell her this, when she cut me off.

“I know what you are thinking you little cock sucker!, but its not for me”

With this she got on her knees again and roughly lifted my legs over her shoulders. As she bent to take my jerking cock in her hot mouth once more, I felt something cold on my ass.

She began to lube my tight ass hole and then slid one, and then two fingers up my ass as she continued to bob on my cock.

When a girl sticks a finger up my ass, it always makes me cum bigger. I don’t know why. And as much as I wanted to suck Jamie’s cock until she came down my throat, the way she was making me feel made me lay back.

All of a sudden, she pulled her mouth from my cock and assumed a more upright position.

As I realized what was about to happen, I opened my mouth to protest, but it was too late.

“Here bitch, we both know what you really need” she said through gritted teeth.

With these words, she rammed her rock hard rod into my tight ass. Generous lube and some finger excercises had loosened me sufficiently so that the first cock up my ass slid in without too much trouble.

The pain was intense, but then faded to a dull ache, and then a delightful tingle. As she began to thrust, the tingle turned to the most intensely hot sexual pleasure I have ever known.

Jamie continued to fuck me, swearing at me and calling me names all the while. I had already figured out that this was how she expressed herself when she was really into the sex, and honestly it just turned me on more.

After all, wasn’t my fantasy to be dominated by a hot shemale? Well it was happening, and it was better than I had ever imagined.

As her pace quickened, I knew she was close to coming, and actually, so was I. Jamie had wrapped her hand around my cock and jerked me in time with her thrusts. I could feel the cum began to rise up in my nuts and threaten to burst free.

Just when I thought I couldn’t take any more, Jamie pulled out of my ass, leaving me feeling empty.

“but..but” I stammered.

“Shut up and lay down on the floor” she commanded.

I did as I was told, and she climbed on top of me in the classic 69 position.

She grabbed my cock and told me to “swallow my cock you little cum loving bitch, and you better not cum until I do”

With that, she swooped down on my cock and began bobbing her head up and down like a piston.

I wasted no time. I peeled the condom she had somehow slipped on from her cock and directed that beautiful piece of meat to my hungry mouth.

I came close to cumming many times. A beautiful woman sucking my cock, and a beautiful cock in my mouth. I was in heaven.

After a very few minutes, I felt her tense up, and sure enough she began to shoot hot, thick ropes of cum down my throat. As soon as the first shot hit my tongue I started to shoot my own load in Jamie’s mouth.

We spent some time licking each other clean and then we cuddled next to each other on the floor, pulling a blanket across our bodies.

“Sorry about the way I talked to you, I cant help it when I get that turned on” she said softly.

“Don’t you dare apologize” I replied, “you are everything I have ever wanted in a woman, and more. I wouldn’t want you to change a thing”

She smiled and said, “You never had a cock in your ass before did you?”

I admitted that I had not, but assured her she could repeat the lesson anytime.

Jamie stayed with me in my hotel until the job was over and I went home. She taught me many many many things, and I will never forget her. I tried to get her to come home with me, but she refused, saying she needed to be near the city.

On her part, she tried to convince me to stay in New York, but I had my own life to go back to.

My life has changed forever now. I still date women, but the only women I want to be with are the ones with nice big dicks.

My dream is to find a shemle lover to spend the rest of my life with.

Are you out there?

Report Story

byThrockmorton© 10 comments/ 137506 views/ 12 favorites

Share the love

Similar stories

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

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

heartHumbled_Slave, aeon7124 and 10 other people favorited this story! 

Recent
Comments
by Anonymous

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

There are no recent comments (10 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (10)

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

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:

   Cancel