My Lover, The Transsexual

Story Info
Title kind of says it all.
1.7k words
4.27
21.2k
17
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

We had been FWB for a few years. Her name is not important, but for this writing, I will call her Marie. We had just spent the day doing what we loved to do. Some fucking, some sucking, and we were lying in bed, her head on my chest.

She asked me if there was anything I wished for at that very moment, and I said, yep! That it would last for a very long time!! I asked her the same question.

She said, "Since getting to know each other's deepest dark secrets, she would love to have a real cock to experience fucking my ass and cumming in my mouth."

I said, well, that would be special, and I would love that. Should I get a tattoo that reads "Marie's personal cock whore?"

She said, "I already scheduled that for tomorrow!" "OHHHHH! Ok." Was the only response I had, along with a chuckle.

She laughed and said no, she knew how opposed to tattoos I was (20 years in the Navy and not one tattoo), but a personalized license plate would work! We laughed together.

It was pretty late, about 2 or 3 in the morning. We had been at it for about 20-22 hours at that point, so we needed to recharge a bit. We drifted off to sleep.

When I woke up, she was just waking up, too, kissed me on the cheek and mumbled something about having to pee.

She got up, stumbled towards the bathroom, and I was just lying there, eyes closed, adjusting to the dim light in the room when she let out a blood curdling scream. I jumped out of bed and ran to the bathroom, but she wouldn't let me in.

All she kept saying is, "what the Fuck? What happened to me???????" I kept begging her to let me in, was scared to death she was bleeding to death, or something. Finally, after a few minutes she opened the door, staring at me, and right there she had the nicest cock I had ever seen! It was magnificent. About 10 inches long, limp and at least 2.5 inches in girth. I was like, "uh, baby? Is this a new strapon you got for me?????" She lifted it up to show me the biggest balls I had ever seen, and showed me it was really attached! WOW, I thought!! I looked at her, and she was about as white as a sheet, so I took her hand and led her back to bed. I turned on the lamp by the bed, and I couldn't take my eyes off it. It literally touched the top of her knees.

We started talking. I said, "but, baby! Wasn't it just last night you wished for this???"

"Yes, but not such a BIG one!! I thought, you know, average? 4 - 6", maybe 1.5" in diameter!"

I commented, "Well, this is what you were given, so I guess we have to accept it and make do with the cock ya got!"

She said, "Yeah, I guess so. So, what next!?"

"Ummm. I don't know! You will need some time to get used to it, for sure." Suddenly, my baby was a VERY SEXY TRANSEXUAL!! Ok. I can deal, it's always been a fascination to me, what it was like to be one, to fuck one, etc. Any man that says otherwise is LYING to himself. I promise! A chick with a dick???? Best of both worlds, I hear. Anyway. We talked for a few minutes, and she said,

"well, if we are going to get started, then you get started by sucking this monster!!" She began to stroke it,

and I said, "Sure, but I want to watch you stroke for a few, see just how hard it gets, along with how much longer it stretches." She began to stroke it up and down, really slow strokes, stopping at the head to rub her fingers across it. "I wonder if I could suck it myself, since you don't seem so interested, now that I have it!"

"Oh, no, I am very interested. This is just as much a turn on as anything we have done!" She said, ok, and kept on, and it grew probably another inch or 3. When she bent down and easily took the first 2 - 3 inches in her own mouth, I reached up and replaced her hand with mine, stroked it for her for a few minutes while she watched, and she said,

"That's pretty hot to watch, too!" I leaned forward and ran my tongue across the head, and slid the tip inside the pee hole!

She jumped and said, "SO, that's what that feels like! Nice, like a small zap of electricity!" Yep, and I kept on, gradually slipping the head past my lips, which was an accomplishment it was so big. She gasped, laid her head back, and her eyes rolled back in her head, and she closed them softly. I still think she was peeking. I began to take it deeper and deeper into my mouth, eventually, it slipped into my throat.

She raised her head, and said, "OMG, FUCK, baby!" I had more than half in my mouth and throat! I kept inching it deeper, and deeper. I would slide it back out, wiped the tears away from trying not to gag, and stroke it to get my spit all over it.

As I stroked her enormous cock, a nice bead of pre-cum appeared on the head. She asked what that was, and I had to tell her! LOL. She was more used to licking it off men's cocks, now she had one of her own and wasn't really ready for that! I stuck out my tongue and licked it up like candy, and immediately started where I left off. Again, her eyes rolled back, and she closed her eyes. In just a matter of a few minutes, I had her all the way in, and was even licking her balls with her cock still buried in the back of my throat.

She said she thought she was about to cum, and I felt the gorgeous beast pulsing in my mouth as she unloaded every drop strait into my stomach. I waited for it to stop, then began a normal blow job of up and down, until I was sure I had drained every drop from that beast!! I pulled her out, leaned down and sucked on those huge balls of hers for a few minutes, waiting on her cock to subside, but it never did. It remained hard as a hammer.

She kissed me deeply, and thanked me for the wonderful blow job, and said she could only imagine what it was like, before. Now, she had experienced her very own, and she understood. She continued stroking her cock as she reached over, pulled out the lube and put it on the bed! I knew exactly what that meant, and I rolled over on my stomach. She them placed our harness on me, drew up the straps so I was WIDLY spread open for her, leaned in and gave me one of the best rim jobs I had EVER had.

"I can't wait to fill this with cum, now!!"

Opening the bottle of lube, she poured a generous amount at the top of the crack of my ass, and let it slowly run down to my balls. She had placed a pillow under my stomach, so I was in the perfect position for her. She worked the lube in my ass with one finger, gradually increasing up to 4, to make sure I was GOOD and ready for her. She lubed up her cock, then leaned over and asked if I was ready, and I said, OH, yes!!

She rubbed her cock head up and down the crack a few times to make sure my ass was good and lubed, along with her cock. I felt the head at my entrance, and with one good push, she was in. Slow, little strokes with the head at first, gradually increasing depth. After a few minutes, I felt her balls hit mine. She stayed like that a few minutes.

I knew what that pause was for. She didn't want to cum so soon, and she was getting ready for the pounding of a lifetime. She licked my ears, chewed on my ear lobes, even played with my nipples while she rested a few. Then, she slowly pulled out, leaving just the massive head inside.

"I never dreamed it could be like this, baby! Your ass is SOOO tight. Well, I have nothing to compare it to, but it FEELS tight!"

"Trust me, baby! That cock in this ass, it's TIGHT!!"

Buried to the balls, again, she paused, once more. I asked her "are you ok, baby????"

"I am BETTER than ok!!"

From that moment on, all bets were off! She fucked me like that for the rest of the day. I could feel each time her balls smacked into mine, rather hard, at times, but I didn't mind! SHE was getting into the role of a "woman" with a nice, REAL cock!!

Finally, she said in a kind of whisper, "I'm going to fill your ass, now!!"

"Go for it, baby!!" A few more good, hard pounding strokes and she did just that! While she was cumming and STILL fucking me, her cum began to ooze out and run down my balls and onto the mattress! She just kept going... And cumming!

Eventually, she collapsed across my back, panting, sweating, and said "that is the most incredible thing I have EVER experienced."

"I am SO very glad, baby!! Can't wait until she is ready to do it all, again.

"That will be in about 20 - 30 minutes after a short rest!

And, true to her word, she fucked me like that the rest of the day, and I was in heaven!" It was when she had gotten dressed and told me she had to borrow my underwear (she normally went commando) to hide "the monster", as we started calling it that she told me she had to go home and try to explain this new development to her husband, that the day turned gloomy.

Well, her husband wanted no part of it, and that evening, though upset and crying, she was back in my arms.

We have been happily together ever since, some 20 years later, and yes, she still has that magnificent monster.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
ShortyMacShortyMacabout 2 years ago

WOW what a hot story. Use to have a girlfriend way back in the mid 1970’s ( real girl) that was a great fuck. If she could have grown a cock of her own I’d have really been so in love with her. She had a perfect body, she loved sex, she was bi, ( though she never shared another girl with me) AND she was so open that she was a NUDE DANCER. We both worked at the same club, and dancers would rotate between our 3 clubs all night long. She didn’t rotate as she was our “Lobby Girl.” Once when the car was late she had to go on stage. The dancers handed me (the DJ and Light tec) their music they wanted to dance to. She forgot to write down which cuts of the record she wanted to dance to. I had to go back stage to find out what cuts to play. She was so turned on we fucked right there on the steps leading to the stage. After a we finished our quick fuck she went on stage with her pussy full of my cum. What a turn on that was for me.

Client8Client8about 3 years ago
Groovy

Just the answer to EVERY man's fantasy. I liked that it was very loving and not the usual "honey I now have a bigger tool so I'm going to beat you up with it." I'm not one to dis woman empowerment, but I like a mutual appreciation much better.

Share this Story

Similar Stories

Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
More Stories