Payback Sucks... Literally

Story Info
The story of a womanizing man who taste of his own medicine.
9.9k words
4.24
50.6k
39
11
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

It was just another normal day at work, when a call came in that required me to drive out to one of our more remote sites. The drive would take me about 90 minutes so I grabbed a good playlist off my iPod and hit play.

As the music played I sang along, danced and didn't have a care in the world. As I sat at the traffic light to get on the interstate, a cute girl pulled up. I nodded my head to her as a way of saying "what's up?"

Her window began to roll down. I asked for her number, she complied and I stored it in my phone.

Little did I know, this would be my downfall.

I arrived at the remote site and performed the maintenance that was needed and drove home from there. On the way home I texted her.

"Hey Abby, this is James. I got your number at the light by the interstate today."

"Hey James! How are you? I didn't think you would actually text me."

"Why wouldn't I text a good looking girl like you? I think we should go out sometime to get to know each other. See where things go. What do you think?"

"SURE when? I am free tonight if you want?"

"OK, want to just hit up Starbucks in town?"

"Yeah that works, what time is good for you? I am free after 6:30."

"7:15 OK?"

"Sounds good I'll see you then! I have to get back to work now."

I was off work early for the day, so I decided to take a nap before my shower.

When I awoke, I climbed in the shower and made sure to shave and trim my body hair as necessary. First I trim my face, get my beard looking good, and then shave my chest and stomach before trimming my pubes back to a 2 guard on the trimmer.

Just as I finished scrubbing myself down and washing my hair my phone rang, it was Abby.

She called to tell me she would be about 20 minutes late. I didn't mind this; it gave me a chance to have a shot at the bar across the street to calm my nerves.

It was about 7:20 and I had finished my shot, so I walked across the street to Starbucks. As I walked in I saw there were two of the comfortable cushioned chairs available, so I made sure to put my hat on one and keys on the other to claim them.

I walked up the counter to place my order, with the goth kid behind the register. I place my order for a Venti Chai Latte with a double shot, paid and moved to the end of the counter to wait for my drink. When I was handed me my drink, he said something in gibberish that I couldn't understand. All I could think was how weird that type of people are.

I sat down to wait for Abby and started to take a sip of my drink as she walked in the door. I got up, greeted her and told her about the seats I was able to claim for us.

She ordered her drink and the same guy made that one too...but no gibberish this time.

We really enjoyed our date that night, it ended with a small kiss and hug, then parted ways vowing to text later that night.

I went home, but stopped for a 6 pack on the way. I opened it before getting home and finished the first one while walking in the door.

While I sat on the couch my phone went off, it was Abby again, she was asking if she could come over and hang out instead of texting. Her roommate had her girlfriend over and it was just uncomfortable to be home while she could hear them roll playing in the bedroom.

I laughed and said "Sure!"

I wasn't going to tell a hot girl she couldn't come over my place to hang out, what was I crazy?

She arrived at my door about 5 minutes later, I was perplexed with how quickly she got there, but maybe she lives in one of the neighboring apartment complexes.

As she walked in the door, she handed me a bottle of tequila. I now knew it would be a fun night!

We made a HUGE pitcher of margaritas and sat on the couch, I put on HBO just for background noise while we talked.

I found out she was 22 years old, only 4 years younger than me. She is one of 3 kids, all girls. Parents divorced. The basic information.

The night wore on and our soberness disappeared, we began getting closer and closer on the couch until our lips were connected and we were making out, followed by groping each other over or clothes.

She took her finger under my chin and led me to my bedroom that could be seen off the living room. She walked backwards and sat down on the bedside bringing her face to my waist height then unzipped my jeans.

After pulling my jeans to my feet and lifting my shirt she pulled my dick from its boxer brief encasing and placed it in her warm mouth.

It was still semi-flaccid until this point when she took it all the way to the base and licked the top of my sack with the tip of her tongue. As she deep throated my almost hard cock, she started to gag while it hit the back of her throat.

I placed my hands on the back of her head and fucked her pretty pale while tangled in her long blonde hair.

Thrusting harder with each stroke, I can see the tears welling up in her eyes but I don't stop. I can feel my shaft start to pulse and my balls tighten as I unleash a huge load of jizz down her throat and in her mouth.

She looks up at me in disgust, pulls her mouth off my dick and says

"You should have warned me, I don't like to swallow!"

I pushed her back on the bed and pulled her tight black yoga pants off of her, exposing her pink cotton thong. Before delving my tongue into her sweet wet abyss, I pull her sweat-shirt and tank-top up to see her bra shackled breasts and release them from their containment.

They must have been at least a C!

I place the left nipple in my mouth and flick it with my tongue getting it erect but at this point she places her hand on my forehead and says

"maybe we've gone too far. Why don't we just lay here and cuddle."

I comply with her request and lay next to her. She starts to kiss me and I can taste myself on her breath and in her mouth, I am disgusted and pull away.

That was the last detail I can remember of the night.

The next morning I wake up groggy from all the tequila and beer I drank the night before, and look around the bed for Abby. She is nowhere to be found, but all of her clothes are lying on the floor neatly folded in a pile right next to the bed.

As I sit up, I feel a heaviness on my shoulders that doesn't feel right, but I ignore it for the moment, because I can't find the hot girl that I was going to eat out before I presumably fell asleep.

Once sitting erect in my bed, I reach across myself to scratch my arm, but I am impeded by a large mass. I look down to find that I have grown boobs, overnight! They are MASSIVE! From first guess I would think they had to be at least a DD cup!

Not sure what to think I lay myself back down and try to compose my thoughts.

"What happened after I passed out?"

My first instinct was to go to the living room, get my cell phone, text Abby to see where she went. Maybe see if she can tell me what the fuck happened!

As I get up, I feel very top heavy, trying to adjust to my new chest appendage I also feel my hair brushing on my shoulders and mid back. As I unsteadily walk, I feel as though my balance is off all the way around.

I am pissed off!

As I stumble into the living room I pass a mirror that I usually look into from the top, I now only meet the middle of and realize I am not nearly as tall as my 6'4" frame once was. I grab my phone and walk into the bathroom.

I stand in front of the toilet and relieve my bladder. It is at this moment, while piss runs down my leg, I look down to see I no longer have a penis and in its place is a small neatly trimmed mound. A pussy.

I find Abby's number and hit call. While I hear the phone ringing, I think of what I am going to say...She answers; I respond with "Abby?" At this moment I don't recognize the voice coming from my mouth.

"Yes, how can I help you? "

"Abby it's me, James, from last night!"

I hear her giggle on the other end of the phone and this irritates me.

"What the fuck did you do to me? How did this happen? What the hell! Why do I have tits? Where is my cock? Why am I short?

"Well you see; I have these pills that you need to take one of each type..."

"And what you fed them both to me after I passed out drunk?"

"Not quite. One was in your drink at Starbucks. I know the guy who works there and he broke it into your latte. He's done this for me on a few dates before. I came over last night to see if you deserved to have the 2nd one. With the way you treated me during that blowjob, I decided you should get a taste of your own medicine, and know what it's like to be forced to do things that aren't that enjoyable!"

"So you turned me into a fucking chick? You made me a fucking chick! What the hell is wrong with you?? How do I fix it?"

"You have to be nice; I am not going to help you if you act like this. By the way, you might want to go look in the purse on the floor in your room. You might need it in a little while."

"Why? What is in there?"

"Womanly products. You will need a tampon or a pad, whatever you're more comfortable with in about five minutes."

"What? I am going to have a period?"

"Yes you are. And it's not going to feel good. The first one is always the worst!"

"Whatever. You're bluffing!"

"You have five days of bleeding, and then you ovulate and will have three to four weeks to convince me to help you"

At this point I can't hear any more, I hang up the phone, and go to the bedroom. Suddenly I am hit with a shooting pain in my stomach that I can barely handle. I double over in pain, and the weight of my breasts pull me to the floor. I fall over. Lying down I feel something slowly starting to flow from me. So I grab the purse and one of the pads inside it. I open it and place it in the underwear at the top of the pile of clothes and put them on.

After a few moments of dealing with this incredible pain, I am able to bring myself to my feet and continue figuring out what to do.

I go to my dresser and try to find the baggiest clothes I own, but to no avail, I still look like a chick in a dude's clothes.

Should I embrace this or fight it?

As I consider this I realize that if I embrace it, it will most likely please Abby more, and she will be more willing to help me change back. So I pick up the clothes she left on the floor, and start to size up how they will fit me.

First the underwear that I have on needs to be adjusted and this pad isn't comfortable at all, but I assume none of these items are. I suppose I can try the tampon.

I reach into the purse and grab out the box of tampons, at least she was prepared for me to need both. I open the box and pull out the small wrapped item, and begin to try and discern how to operate it. I tear open the wrapper and hold the small plastic bullet shaped object in my hand then pull the stick back until it clicks.

At this point it has now hit me, it will have to be inserted into my newly formed vagina and this is probably best done in the bathroom.

I walk to the bathroom and sit myself down on the toilet seat, pull my underwear down and spread my legs. Leaning forward I realize how much these tits are going to be getting in my way, but work my way around them to spread open the lips of my mound and slowly slide this device inside me.

It's an odd feeling having something inside me, but it's a nice one to be touching this ultra sensitive vagina too.

As I push the plunger in, I feel the small cotton tampon slide inside me and pop out of its casing and slowly pull the plastic out. As I do this I feel the string tickle me, and it sends a spark through me, that I have never felt before. I grab a piece of toilet tissue and begin to wipe the bloody mess that is now my vagina. While the tissue cleans me, it also brings back that tickle. I will have to explore this later...it's interesting.

I stand up and go to get my coffee, I need it this morning. As I walk I notice a bit more of a sway in my hips that wasn't there before.

Just after I pour my coffee my cell phone rings. It's Abby again.

"Hey James, it's Abby."

"I know who it is. This is a cell phone; it tells me who is calling."

"You don't have to be rude; I am just here to help you,"

"Help me!?!?! You did this to me!"

"Well you will not get your dick back again if I don't help you."

"Fine. Why are you calling me?"

"I just want to give you more information about what has happened to you and what will be happening to you. The first step was you passing out last night. I watched the whole process happen last night, and I must say; you are sexy! But anyhow, after the change occurred, I left. This morning you got your first and maybe your last period. Who knows? In about 2 or 3 hours you are going to pass out again, and it will make the final mental changes that are required for you to function. So don't go anywhere yet. With those mental changes will come basic adult female knowledge, like makeup, clothes, and general abilities and urges that women have."

"Urges?"

"Yes, you will have urges. You will still remember being a man, and will know all of the things about yourself and who you are, but will act and respond as a normal adult woman would."

"What do you mean?"

"Instead of naturally being the aggressor in a situation, you will be more submissive. You will have more self control. More emotional thought."

"Jeeze! Great!"

"Anyway. After three to seven days your period will end, you will ovulate and the real countdown will start. You have until you have another period to convince me that you deserve to be a man again. If you start to bleed again, you will bleed once a month for the rest of your life. Well I guess not once a month...if you use birth control or get pregnant."

"I can get pregnant? Are you fucking kidding me? WHAT THE HELL! How would I get pregnant? I won't be fucking anyone...let alone GUYS!!"

"Yes, actually you can get pregnant as soon as your period ends. That would cancel out all of this, and you would be stuck forever. Nothing I could do from there. And I wouldn't say you won't be fucking anyone. Your new urges might change that!"

She takes a long pause, and then continues.

"Anyhow you will always remember what it was like to be a man, but as time passes you will only identify as a female. Have you picked a more feminine name? We both know James won't work."

"I hadn't thought about a name, and I don't know what to think about all of this. I am just lost right now. But If I am stuck this way, I guess it is a good thing that all of this will essentially come naturally so I don't have a learning curve. I am still really mad at you though."

"Well your feminine though process is already working, you've started to calm down. I am sorry you're mad at me, but this can make you a better man in the end. If you get to be one again. For now, just put on some comfortable clothes, lay on the couch and relax until you wake up later. Maybe if you're lucky I'll be there to help when you do."

"Fine, I guess."

"And pick a new name! I'll talk to you later."

I really hadn't thought about a name until she brought it up, I guess I didn't want to admit I would be like this for a while or that I would have to see people like this. I guess I will go with the name Jenny, it starts with a J and hopefully it won't take a lot of getting used to. How am I going to work for the next few weeks? Maybe I will use up all that vacation time that I save from never going anywhere.

After pondering all of these things I head back to the bedroom to follow instructions and get into comfortable clothes.

I go for my dresser and put on my sweatpants but they are way too long. I must be a foot shorter! I surrender and grab the yoga pants Abby left on the floor.

Without even considering my own clothes again, I pick up the bra and tank-top too. I throw the bra on my shoulders and place my new boobs in the cups, as the cloth brushes against my nipples I begin to feel aroused, my new genitals start to ache and pulse.

I run my hand down my smooth stomach and into my pants to feel around and see what is going on down there. I have short trimmed pubic hair, just like I trimmed mine the night before. I feel a soft mound that is familiar to me, but so strange.

I use my ring and index fingers to spread the mound and lips open, while exploring with my middle finger. At the top I feel a bump that when touched sends me into orbit! That must be my clit, just below that is a fold where the lips meet and just below that an opening.

Although I really enjoy rubbing my clit, I slide my middle finger inside the front of the hole and work it in and out. I am amazed at how good this feels and how sensitive it really is. I can feel every bump and groove in my finger, even the edges of my fingerprint. I'm starting to shake as I feel a rush come over me. I feel as though all the blood in my body rushes to the surface and all the muscles in my legs and stomach tense up then the feeling is gone in an instant.

"Did I just finger myself to an orgasm?"

I guess that is no different than playing with Rosie Palm and her five friends. As I slide my hand from my pants, I am quickly reminded that I have my period by the blood now on my fingers and as the cramps pick up again.

I find myself doubled over in pain. I wipe my fingers off on the towel hanging next to me on the door and continue to fiddle with the bra. I can't reach the straps to fasten it. How do chicks do this? I just can't reach! So I grab my phone and Google it.

After reading a few different pages, I learn the easiest way, is to clasp the bra in the front, spin it around my body and put my arms through the holes. Then bend over and jiggle the bra to get them in place. I guess I am bigger than a C, because I am more than clearly spilling out of Abby's 34C. Once I master the bra, I pick up the tank-top again and put it on. Now I am more comfortable and ready for this nap that I am apparently going to be taking. I walk to the living room and lie on the couch, turn on Sports-Center and just prepare for whatever is coming next.

Still lying on the couch, I start to wake up, but before I open my eyes, I just hope that it is all gone and was just a bad dream. I squint open my eyes and see the fuchsia tank-top and know this isn't the case. I take a deep breath and feel the weight of my breasts on my chest and am brought back to this nightmare of a reality. Mentally I feel about the same, but have this pressing feeling in my lower abdomen. I head to the bathroom and before relieving myself; I remove my tampon, wrap it up in toilet paper and toss it in the trash. I pee, and wipe. All without thinking about it. How did I know I needed to do that? I guess Abby was right, I just knew.

If I am going to be like this for a while, I suppose I should go out to a store and get some make-up, clothes and shoes and a few bras that actually fit.

First thing is first, I need to clean myself up and take a shower. While allowing the water to run down my skin I start to play with my nipples again, and then lead my hands back to my pussy. While I finger fuck myself I quickly pull out and gently slap my neatly trimmed mound, this gets my clit really tingly and I slip one finger back inside me and use my thumb to rub my clit.

With my other hand I am pinching and pulling on my nipples and this all brings me to another orgasm. This one more intense and longer lasting, It causes my knees to buckle, my eyes to roll into my head and a loud panting moan while I drop to the floor of my shower. I guess if this is something I can do to myself, being a woman won't be too bad for a few weeks.

After getting cleaned up, re-inserting a tampon and wrapping a towel around my chest, I head back to the bedroom to see if there is anything clean that I can fit in to go shopping.

I find that old pair of sweatpants, cut the bottoms off to turn them in to a capri, throw an old t-shirt and hoodie on, and grab the one pair of sneakers that Abby left behind. I look in the mirror and think to my self, god I look like a hot mess! How can I go in public like this? And with that, I again realize that nap really did change the way I think.