Tangled Web

Story Info
A beautiful woman, and a seductive trap.
1.7k words
2.79
32.4k
8
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

One fateful day I met a girl that changed my life forever. She was especially good looking that day in fact, with nice long legs, well toned curves, long dark hair, and pouty red lips. I never would have known. I struck up a conversation with her, as the PUAs taught me to, and before long we were sitting down alone at a table with coffee and snacks. We talked for a good half hour before she happened to look over to the waitress for a second at just the right angle. There was no denying it. She had an Adam's apple.

Lots of men would have left at that moment, but I still thought she was hot, and I thought I could get over it for some decent anal. Not wanting to publicly embarrass her, I very quietly called her out on it. She was a lot more calm about it than I thought she would be, just mentioning that I was still there, so I must not be too bothered by it. I thought about this for a moment, and realized that I wasn't really bothered. I still wanted to have sex with her.

She was great in bed. A real giver. They say that blind people learn to use their other senses better. Since she only had one hole, I guessed that she must have learned to really make the most of it. While on all fours, she clenched against my cock, and slammed back into me as I took her from behind. When I came, I felt completely empty, like I didn't have a single sperm left to blow inside her. From that moment on, I had convinced myself that I was in love.

It wasn't too long before we found ourselves in a real hand holding, regular sex having, "No, you hang up" relationship. She loved to talk, and most times I just let her. Since she had made permanent physical changes to her body that bound her to the LBGT community about as intimately as anyone could be, that's one of the topics we ended up talking about the most. In one of the first big discussions we ever had, we talked about the different types of transsexual. She was a pre-op male to female transsexual, which meant that she was born a guy, she had hormone therapy and cosmetic surgery to look like a woman, but she still had a penis. A post-op male to female would be someone who had been through everything she had, and then decided that she wanted a vagina instead of a penis. Doctors nowadays can do that pretty well. I couldn't even tell the difference on some of them.

After a picture show of some totally nice looking pussies, she told me that she was never going to get rid of it. She wasn't sure how I felt about it, and understood if I couldn't handle it, etc, etc, but she wasn't ever going to have a vagina. I said I was fine with it.

We had lots of other discussions like this, and most times I ended up being so amazed at how hot she is despite being born a guy. That thought always made me appreciate her all the more, and almost always resulted in her ass getting filled. It took me a little while to get over it, but in time I started to just completely accept the fact that I was dating a transsexual woman. With that acceptance came the thought that there might be things I could do with her that I couldn't do with a natural girl. Up until this point, I hadn't even done anything with her cock. It was just kind of there when I fucked her, but one day I just decided to go the distance. I sucked her cock and opened my ass for her insertion. I didn't even cum that day. It was all about her. I was trying to cram all my past due reciprocation from 8 months into one cum smeared day.

The next morning, my ass hurt like never before, but then I thought back to why it hurt and I couldn't complain. I willingly put another person's penis inside my ass and I liked it. There's a sentence I wouldn't have been able to see myself ever before saying. It was true though. We had some after glow pillow talk that morning. It was then that she hit me with something that I couldn't have expected. She explained to me that last night she realized she needed a vagina. I was floored. I had spent all this time getting used to her with a penis, and imagining myself possibly even just living without pussy. I thought I might be able to do it too. All this kind of thinking felt completely pointless though, when she hit me with "Oh no, not for me. I meant for you."

I couldn't even believe it, and I asked her to repeat it just in case I had heard her wrong. It was after she repeated herself that I realized why we spent all those hours looking at fake vaginas. Last week she showed me a whole new set of them. She said that she would understand if I didn't want to do it, but that this was like a life dream of hers. She said that she was completely heterosexual in a way that only a transsexual could be. She needed to have someone with the body of a man and the genitals of a woman to complement her. She said that she couldn't be happy without a pretty pussy to fuck and a handsome man to love. I should have left her and moved on, but I was young and so completely in love with her that I thought we'd just get married and spend the rest of our days together, so I finally agreed. I couldn't even believe I was agreeing to this, but I asked her to find me a doctor. She did so much research into this that she had the perfect doctor already picked out who would just give me the surgery with no hormone replacement and no questions.

She wasted no time in setting up an appointment. I'd have to travel to Bangkok to get it, as the doctors here wouldn't even do this without giving me a full transition. The consultation was in less than a week and the initial surgery could be done in two. The day finally arrived and I couldn't help but masturbate before I left. I watched some genetic girls take turns eating each other out. I went in with my head low, but I consoled myself by thinking that it's all for the hottest sexiest girl I've ever known. If she had never had a sex change, I'd never have gotten to enjoy the sexy body she has, so she had a sex change for me, and I was about to return the favor.

It was over pretty quickly, and afterwards it didn't hurt as much as I thought it would. It looked ugly at first. Just a bloody hole, but after the follow up surgeries and some time to let it heal it started to look really nice. I couldn't help but admire it in the mirror. I had a hot little pussy, and all the fear and confusion went away when I thought of my hot tranny girlfriend banging this pretty pussy.

I sat on the bed stroking my brand new clit, just waiting for her to get home. I was excited even. The more I thought about it, the more I couldn't wait to feel that cock in me. When she got home, she saw me playing with my new toy and pulled down her panties to reveal one of the hardest erections I had ever seen. She was about to give my pussy the pounding of a lifetime, and my mouth was watering at the thought. She came over and very slowly lubed up her thick cock. She played with it a little, just to tease me. When she had almost emptied the bottle and rubbed it all in, she came over to me with lube dripping everywhere. I was on my back, and opened my legs in sweet anticipation. She grabbed my legs and made sure the position was just right for the insertion I so eagerly awaited. Then she shoved it in my ass.

She plowed my ass like I'd never even dreamed it could be fucked. I was pissed at her for getting me so worked up just to fuck a hole she could have fucked without my life altering sex change. While she fucked my ass, she explained that she was never going to fuck my pussy. She just wanted to look at it while she fucks my ass. That's it. It's nicer to look at than a floppy penis. I had changed myself into something that no other woman would ever date, and she wasn't even going to play with her new toy.

After she came, she pulled out and reached into her purse. She handed me a list of men's names. I asked what it was, and she explained that it was a list of all her other lovers. Apparently, she'd convinced all of them to get their penises removed too. This was then to be my support group, and her list of fuck buddies. She added my name to the list and left me with sperm still dripping out of my ass. I cried myself to sleep.

She still comes over and fucks my ass from time to time. I don't fight it, and I've learned not to even talk to her. She just comes in completely unanounced and expects to ass fuck me. If it's not clean, then she smacks me and waits for me to get it clean. She never says a word to me. After she cums, she just leaves. At least she uses lube. I think she's got a new boyfriend she's working on now. I can't bring myself to warn him. Ever since I had it cut off, I just can't defy her anymore. Probably the lack of testosterone. Besides, if I piss her off, I might not get any sex anymore and then I'd be alone forever.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Client8Client8almost 2 years ago

Ouch@ is all I can say. Thus is the saddest story ever, and not in a good way

AnonymousAnonymousover 12 years ago
Haha!

Pointless. But fun.

AnonymousAnonymousover 12 years ago

umm... ok...

AnonymousAnonymousover 12 years ago
What an absolute

piece of crap!

Share this Story

story TAGS

Similar Stories

Your Best Damn Girlfriend Ever College shemale encounter.in Transgender & Crossdressers
Her Bulge The woman at the gym has a bulge in her spandex.in Transgender & Crossdressers
Snapped: A Shemale's Story Reject her at your own risk.in Transgender & Crossdressers
What A Man Needs? A guy, a porn shop, and a surprise.in Transgender & Crossdressers
Late Ch. 01 His coach is a stone cold stunner, but too hot to handle?in Transgender & Crossdressers
More Stories