Turned into a Slut Ch. 02

Story Info
Timmy learns about cocksucking.
3.6k words
4.47
128.4k
59

Part 2 of the 5 part series

Updated 10/25/2022
Created 07/01/2012
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

I woke in the morning to Jennifer sucking my cock. She had pulled the sheets off the bed and was kneeling between my legs, licking up and down the shaft. Every few passes she would let it slide into her mouth and wash the head with her tongue. Her other hand was busy teasing at my anus, sliding a little in to massage my prostate. I sighed in pleasure and Jennifer lifted her mouth off my dick.

"Good, you're finally awake. It's almost noon and we have lots to do today."

"What about the blowjob?" I asked gesturing towards my hard dick that she had left.

"Oh don't worry about that, there will be plenty of that later, we have to get going now. I have everything ready in the bathroom for you so get up and get in there," she said, pulling on my hands, struggling to get me out of bed. I reluctantly rolled out and stumbled sleepily after her.

"Here babe, sit down on the toilet. If you are gonna pretend to be a girl you might as well start peeing like one too," she teased, smiled as I flushed red with embarrassment.

"Look Jennifer, I know we had fun last night but I don't really think we should, you know, continue with this," I stammered. Sure last night had thrilled me and I'm pretty sure it was the biggest orgasm of my life but I wasn't at all sure I wanted to be a girl for her.

"Ahh, is Tiffany having second thoughts?" she taunted. "Well I took care of that for you already. If you didn't notice last night I recorded everything we did on video and uploaded it to my computer this morning while you were still sleeping. So, unless you want your friends to see you spreading your ass for me and loving every second of it, you better do as I say. Besides, I was there too and I know you had the biggest orgasm of your life. I did too after all!" she patted my face as I sat there in stunned silence, my mouth hanging open. I was shocked that she would use anything like blackmail to get what she wanted. Especially from me, her boyfriend!

"That's, that's... blackmail!" I squeaked out at her.

"Hmm, I guess technically it is, but it's not like I'm forcing you to do anything you don't want to do baby," she said, as if that made it all right. I suppose in her mind it probably did. "Now quit your complaining and spread this cream over your legs. It's a hair removal cream and will make you slick and smooth like girls should be.

"Fine," I said, defeated.

"I think you meant to say, "Yes Mistress"," she scolded me. "Or would you like me to squeeze these?" Her hand was cradling my balls. I winced as I remembered the little squeeze she had given me last night.

"Yes Mistress," I said, looking dejectedly down at the floor. Jennifer's eyes were filled with laughter as she watched my humiliation.

She helped me spread the cream over my legs, getting all the places I missed. Then she made me bend over as she spread it around my asshole and butt. Lastly, she used a pair of scissors to trim my pubic hair down before spreading a little bit of the cream around my dick and balls. I sat on the toilet as instructed and waited for the tingling sensation she assured me would come.

"We are gonna have so much fun today," she said excitedly. "Let's hit up the department store at the mall first. Well, I'm kinda hungry so I guess lunch, then we get to shop for some clothes." She glanced at her watch. "Three minutes left."

"Jennifer, can we..." I started to say.

"Mistress"

"Hmm?"

"You said Jennifer, not Mistress. You will address me as Mistress when we are in private from now on or I will punish you," she spoke matter-of-factly.

I paused for a second, considering what she said. "Mistress, we can eat at the food court in the mall if you would like.

"Sure!" Jennifer said. "Oh, also, after the department store, I have a surprise for you!" she giggled excitedly, hopping up and down.

"Mistress, my body is all tingling now."

"Alright, wait another minute."

After a minute had past I jumped into the shower and sat under the spray, watching all the hair on my body wash down the drain. Then Jennifer handed me a bottle of shaving cream and a razor and told me to shave my armpits and face. When I was done I got out of the shower and dried off. I went back to her bedroom where I found her lying some clothes out on the bed.

"Since this is your first time, I think we will go a little easy on you. I got some stylish sneakers for you so you won't be wearing heels yet. Also, I bought you a nice pair of tight jeans. I know you secretly want to wear skirts but I think it's a little too cold out there right now for that. Here, put these panties on." She handed me a pair of pink panties.

I was shocked at how they felt as I pulled them up my smooth legs. They clung tightly to my butt and encased my dick in their soft, smooth fabric. I was embarrassed to find myself rock hard already.

"Hmm, we can't have that now, can we? Let me see if I can do something to help you," Jennifer said as she knelt in front of me. She pulled my panties down and licked the tip of my cock teasingly. Then, before I knew what was happening, she wrapped her hand around my balls, squeezing them slightly while holding a bag of freezing cold ice up to my crotch. I admit I let out a most unmanly screech as she did this but I guess it was in keeping with character now.

With her grip around my balls I couldn't do much more than whimper as she held the ice to my dick. When my dick was as soft and limp as it was gonna get, Jennifer pulled out a plastic device I had never seen before. It was shaped like a limp penis and structured like a cage. "This is a chastity device, my sweet Tiffany. I got it for you because I know that little sluts can't be trusted to keep from touching themselves every moment they can," she said as she slipped it over my limp penis, adjusted the rings so it was tight behind my balls and locked the cage with a little lock. "There, now we won't have any unsightly bumps showing up in your jeans and you won't get all hard whenever you see cute guys walking by."

She stood up and kissed me on the mouth. "Mistress, I don't get hard when I see guys," I protested. "This is hurting me, do I really need to have this on?" I asked her.

She stroked my face lovingly. "Yes Tiffany, we need to keep your little dicklet safe in there. Plus we wouldn't want anyone accidentally mistaking you for a man," she laughed as she said the last part.

"Jennifer, I don't like you calling my dick a dicklet or clit, it really hurts my feelings," I told her. I was still that thinking this was all just a game and I didn't want her to know I secretly got a thrill every time she belittled me like that.

Slap.

I whimpered in pain, shocked that she had just slapped me. "MISTRESS," she yelled. "Next time it will be your balls and don't forget about the video." For a second I thought should was going to do it anyways but she suddenly seemed to relax. She smiled and I felt as if she had forgiven me and all was right in the world.

"Baby, if I didn't care about your feelings I wouldn't have put you in my panties with a cock cage on! Now, if you want to ever have any pleasure from that little thing you call a cock again you better be on your best behavior from now on, I have the only key after all!" She giggled, gesturing to a key that was dangling on a chain around her neck.

My pulse raced and my dick lurched, sending a wave of pain through me as it pushed against its confining cage, as I looked at the shining key nestled between the gentle swell of her breasts. I gazed down at the floor as she turned away and walked over to the bed. The last wall of resistance had fallen and I was now her slave. She picked up the jeans and threw them to me. I caught them and put them on, wiggling a bit to get them over my hips. They were very tight and really made my ass pop out. I looked down and sure enough, the chastity belt kept my cock from showing more than a slight bump.

Next Jennifer brought over a bra for me. It was a pink push-up bra with little black polka dots all over and a little black bow in the center. I put it on over my flat chest, struggling to do the clasp in the back. Jennifer giggled at my attempt before helping me out.

She brought over two objects next. They were flesh colored and sort of cone shaped. I realized they were breast forms when she pulled my bra out and slipped them inside. "These should give you a nice little slut rack you can tease all the boys with."

After a few adjustments she stepped back and I looked down at my chest. The forms gave me nice B-cup sized breasts. I was oddly aroused at the sight of them even though I knew they were fake.

I knew Jennifer was still in control of my whole life from now on and I was starting to feel better about my predicament now. Though I still had my private reservations about dressing as a woman, I had to admit that the clothes did feel great on me. Jennifer handed me a shirt to put on.

"This shirt will go great with your jeans and really make your boobs stick out! What do you think?"

It was a black shirt with a sparkly rose decal on the front in a very Goth/Punk Hot Topic style. The back of the shirt had slits cut horizontally down it and I knew anyone walking behind me would be able to see the straps of the bra I was wearing and my smooth back all the way down to the pink panties peeking out above my jeans.

"It looks hot Mistress," I smiled shyly.

Last, Jennifer brought out a long black wig. She dabbed a little adhesive on my head and settled the wig into place, letting the bangs drape over my forehead and combed out the back so it fell smoothly down past my shoulders. The adhesive, she told me, was very strong but would dissolve when washed with a special shampoo, though sweat would not affect it at all. I reached up and tucked the sides behind my ears and flipped a few strands over my shoulder.

"You're a natural at this!" she teased as she helped me brush the hair into place. I blushed at her praise. "Alright, last thing we need to do is put some light makeup on you." She sat me down in front of her vanity and began pulling out the items she would need.

First, she applied a foundation that gave my skin an even tone. Next, she grabbed some eye shadow and began deftly applying a dark purple shade over my eyes with a black frame on the edges. She grabbed an eye lining pencil and sketched it on, highlighting my eyes, making the stunning blue pop out.

"God you have the longest eyelashes," she said as she brushed on some mascara. "Any girl would kill to have eyes like yours." I could tell she was jealous of my eyelashes and I'm not ashamed to admit the knowledge made me happy.

She gave my lips a dark reddish purple color with a lipstick that made my lips swell up slightly. Last, she used some tweezers to even out the bushy eyebrows I had, forming them into delicate arches that gave me a permanent, girlish look of surprise.

"There," she said as she let me look at the finished product in the mirror. I was shocked to see the face of a beautiful young seductress looking back at me. My eyes had a hypnotizing look to them and my lips looked like they were dying to wrap themselves around a nice hard cock. "I think we are ready to go now!" she squealed and pulled me up into a hug. My cock strained in its cage when I felt our breasts bump into each other. "Here is your purse," she handed me a small pink and black purse that tucked up under my arm. Your socks and shoes are over there. I'm gonna pop into the bathroom and when I come out we're gonna be off!"

While she was gone I slipped on the ankle socks and sneakers. For the first time I realized that I had the perfect body for this. My slender built looked very feminine in these tight clothes. All I needed was curves in the right places, which the breasts forms helped with, and I totally looked like a smoking hot sexpot. I was suddenly very eager for our shopping trip to the mall.

On the way to the mall Jennifer let the car's top down. I was glad for the adhesive used to hold my wig in place because the wind was blowing my hair around like crazy. Jennifer was laughing and joking the whole time, teasing me about my looks and occasionally running her hand up my legs. It must have looked to anyone driving by that we were simply two girlfriends out for a good time.

We pulled into the mall close to two o'clock. We were both very hungry by this time and our first stop was the food court. I started to head over to the burger stand but Jennifer grabbed my hand and guided me to the salad stand instead.

"Nope, sexy ladies like us don't get to eat greasy burgers. We're gonna have some salads!" she smirked at me. I was thankful that she let me have chicken slices on my salad because otherwise I would have been starving after lunch too.

The whole time we were there, Jennifer kept coaching me on how to act like a woman. She told me to eat slowly, keep my tits pushed out and my shoulder thrown back. I felt like a soldier marching along but for the sexy hip sway she encouraged me to try by placing my feet one in front of the other when I walked.

I was feeling very sexy by now and shocked myself when I would smile and wink at some of the cute guys that were checking me out as they walked by. I took secret thrill in winking at the cute girls too. Jennifer noticed this after the 3rd or 4th time I did it.

"You little tease!" she scolded me. "You have no intention of getting any of these guys or girls off, yet you still flirt back with them! You are such a little slut." I tried to protest but she ignored everything I said.

Jennifer took us to our first destination, a department store, and guided me back to the women's section. We tried on shoes first and after putting on what seemed like a million heels I fell in love with a pair of 3 inch black ones with an opening for the toes to peek out. I knew that with a little red nail polish I could pull off a stunning look. We browsed through the lingerie section after that. I picked up a dozen panties and a few cute bras too.

Next we looked at skirts. Jennifer had me try on a few and model them for her. We settled on a short, blue plaid miniskirt that just barely covered my butt and let my panties peek out whenever I bent over. She took great delight in making me strut around where people could chance by with my chastity belt just barely covered.

As we were browsing through the clothes, Jennifer grabbed a young man who was walking by and asked him for his opinion on my outfit. He told me he thought I looked pretty fucking hot. I batted my eyelashes shyly at him.

Jennifer told him he should take a closer look when he turned to go. He paused, looked at me with a questioningly. I looked at Jennifer, scared, but the look in her eyes told me I should go along with it. I shrugged my shoulders slightly in invitation to the man. He walked closer and started to look me up and down. I could feel his breath on my neck as he walked around me, lightly running his hands up and down my sides.

I could tell that Jennifer was getting turned on by the way she was biting her lip. She looked around, noticed that no one was around, and then pushed us both back into one of the changing rooms. She knelt in front of the man, pulling me down with her.

"Ever wanted to get your dick sucked in a changing room?" she asked him. He just nodded, a stunned look on his face.

When she started to undo his pants I knew I was about to get my first lesson in cocksucking. I began to freak out but Jennifer was expecting this and started rubbing my back, whispering reassuring things into my ear.

"Don't worry baby doll, you're gonna love his cock. Just take it into your mouth like you've always wanted to. All you gotta do is worship it with you lips and tongue," she told me. By now she had his cock out and it was already half hard. It was much bigger than mine. My caged cock throbbed harder at the sight and I knew my jaw was gonna hurt after this. Jennifer brought my hand up to the man's dick. She showed me how to hold it and stroke it up and down.

"Don't forget the balls honey, men love to have their balls played with. Gently massage them to coax that cum out. Make sure you are playing with the shaft at the same time though," Jennifer instructed between mouthfuls of cock. The man was groaning the whole time and precum had already started to ooze out of the head. "Here baby, it's your turn to give it a try," she said, gently pushed my head towards the cock.

I tentatively opened my mouth and swallowed the head of the dick. It was soft and warm and I marveled out how it felt on my tongue. I ran my tongue all around the head, keeping my lips sealed and tight on the shaft. At the same time I stroked up and down, slowly squeezing the shaft, marveling at how hard it was, yet how it was covered in the softest of skin.

After I had got used to the feel of the head in my mouth, I slowly let my lips slide down the shaft. At first I could only take a few inches in my mouth but with the man's hand behind my head and Jennifer pushing on the back of my throat I was able to stuff a few more inches in. My gag reflex kicked in and I coughed, gasped for breath.

"Are you ok in there?" someone outside asked.

We all froze for a moment before Jennifer called out, "Ya, I just had something in the back of my throat." The man snickered at her pun and I blushed.

"OK," the voice said uncertainly and we heard footsteps hurrying away. We all breathed a sigh of relief. Jennifer quickly push me back towards the cock.

"Hurry up and finish sucking him off, she probably went to tell a manager or something."

I renewed my efforts to bring him off, rapidly jerking the shaft as I pumped my mouth up and down. I loved the feeling of his cock in my mouth. It felt wonderful and I didn't want to stop making love to it. I could feel him starting to cum when his balls tightened up.

"Take it all, swallow his cum you little sissy faggot!" Jennifer whispered in my ear, her hands stroking my ass. The man and I both groaned together as he shot his load in my mouth. I gulped down his cum as it splashed jet after jet into the back of my throat. "That's the cum of a real man you are swallowing sissy." Jennifer said to me. I could only groan in agreement. Hastily the man pulled up his pants, tucked his shirt in and hurried off. Jennifer helped me rearrange my clothes, telling me the whole time how I was a natural cocksucker and how I looked so hot sucking that dick. She made me kneel between her legs and lick her clit until she came less than a minute later. I asked her to let me out of the cage so I could cum too but she just giggled.

"I'll let you cum later little cocksucker. I got something special planned for you now." We quickly gathered our stuff and left the changing room.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymous6 months ago

Devious and sorta predictable ….. but no complaints from me!

Another 5 Star 👏👏👏

mattenwmattenwalmost 2 years ago

Nonsense. Who will stop him from going to the police and reporting her for extortion and sexual assault?

AnonymousAnonymousover 6 years ago
I thout I was a straight male....

until I read this story and tries some of the things in it.

Tootight1Tootight1over 9 years ago
great

but fearful of future.

devilspy2001devilspy2001over 10 years ago
You did not read the start of this tale.

Our sissy boy is quickly leaning and now that he has had a real man cock to suck on, he will want more. More thick hard cock in his sissy mouth, and more hot thick real man sperm for his belly. She is training out boy to be a slut for real stud bi men. Even open minded STR8 studs will enjoy fucking this sexy boys mouth. Feeding him the hard dick and hot thick seed he will not crave. I bet his little clit is leaking and dripping in his pretty panties and chastity. I hope she keeps him locked up for longer than a day. Get him begging before she milks his balls dry.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
My Husband’s Birthday Sexual humiliation for his birthday gift.in Transgender & Crossdressers
She Makes Him Kinky girlfriend seduces boyfriend into becoming her slut.in Group Sex
More Stories