Jasmine

By Andi

Published on Apr 22, 2009

Transgender

The following story contains blackmail, bi sexual activity, cross dressing, and sex with minors. if any of the above bothers you please do not read. The following events are purely fictional.

Any feedback would be truly appreciated.

I hope you enjoy.....

My name is Randy, actually it was Randolph Duncan. I am a 35 years old, married to a beautiful woman, had two kids, a son 8 and a daughter 5. I am small in stature, I am 5'7" 150 pounds, short blonde hair, blue eyes.

The following story is the third story in a series about how my life changed over a two week period last June. How I became Jasmine.

Jasmine - 03 - The Shopping Trip

I awoke sometime Sunday Morning, I assumed it was still early but I had no way to be sure. I was lying in my bed, my hands were tied to the bedpost with electrical chords. I was wearing a black and purple teddy with garters and black stockings.

My cum soaked panties were in my mouth and they were tied in place with a stocking. The matching stocking was wrapped around my eyes effectively blindfolding me. I was still wearing makeup and my long red wig.

I had been tied to the bed since 9:30 last night when Sam had tied me up and left me alone. I had been laying there for some time when I heard the bedroom door open.

Soon I felt a hand on my thigh then the hand hit my small soft cock hard causing me tremendous pain. Whoever it was in the room with me must have liked my reaction because they done it again. And again.

I was in extreme pain and in tears. I was struggling against the chords keeping me tied to the bed posts trying to get free. They hit me one last time then stopped.

I felt the person get onto the bed and there hands went under my legs lifting them into the air. The I felt something pushing into my ass. OH GOD NO I screamed into my gag as I felt someone's cock pushed into my ass.

I had never been fucked in the ass before yesterday when it happened twice. This morning my butt was still sore from the pounding I received from Steve and Sam and the guy getting ready to fuck me did not bother to use any sort of lube.

Whoever it was gave no consideration for my comfort, he just forced his cock into my ass and started fucking me. My ass was dry so the friction was terrible and it hurt like hell. I could not figure out for sure if it was Steve or Sam but I figured it was Sam, he seemed to be the more cruel one between the two of them.

He started off slow fucking me with long painful strokes. He still had not said anything, all I heard was moaning and grunting as he picked up the pace. He would occasionally hit my cock from time to time increasing the pain.

He would alternate from abusing my cock and pinching and twisting my nipples. He was fucking me faster now and I felt the cock in my ass get bigger. Instead of cumming in my ass, whoever it was decided to pull out.

I felt him move around. I was hoping whoever was using me was finally going to untie me. He did untie my gag and remove my panties.

Instead of removing the blindfold or undoing my bonds, whoever it was started rubbing his cock over my lips and face. I tried to turn my head but felt it held in place and his cock pushed pass my lips.

The taste was awful. He started fucking my face the way he had fucked my ass. I was having to fight my gag reflex and trying not to throw up as he was forcing his cock deep into my mouth.

It was not long that he pushed his cock deep and started filling my mouth with cum. I had to swallow to keep from choking. He finally quite cumming and pulled his cock from my mouth. He rubbed the tip all over my mouth and face.

He got off the bed and I assumed he got dressed and I heard the bedroom door close. I lay there needing to pee and wondering when they were going to untie me. ____________________________________________________________

Sometime later the door opened again and I heard Megan laughing. "Man, Sam tied you up good."

She untied my blindfold and then started undoing the electrical chords. I started rubbing my wrists trying to get the circulation flowing again.

"Girl you are a mess. I would tell you to clean up but the guys are hungry. You may use the bathroom, then put your panties and your heels back on and hurry to the kitchen."

After using the bathroom I looked at myself in the mirror. I looked terrible. I also had dried cum all over my face. I knew Megan had told me to hurry but I took the time to wash my face.

When I made my way to the kitchen, Megan, Sam and Steve were sitting at the table drinking coffee. I had to fix them omelets like I did the day before.

Megan and Sam are my neighbors and are brother and sister, Steve is Megan's boyfriend.

Megan is a cute 17 yr old.. 5'3" 110 pounds, long legs, brown hair, brown eyes. Perky 34 B breasts.

Sam is her 15 year old brother, he is 5'8" a little over weight, blonde hair, blue eyes. Sam has a mean streak and is way more perverted than any 15 year old should ever be.

Steve was over 6' tall and muscular with blonde hair, He was 22 and a senior in college.

As I served them, Sam and Steve would either swat my ass or pinch and grope it. My stomach was rumbling because I had not be allowed to eat in over 36 hours.

Sam had decided that I need to lose weight and would not let me eat anything. He did allow me to get a glass of orange juice. As I was pouring my juice there was a knock at the door.

I panicked but thankfully Megan jumped up and said that she would answer it. She came back into the kitchen with Johnny following behind.

Johnny was 5'7" with short curly black hair, brown eyes. He is skinny and just 15 years old like Sam. He was wearing a nice black suit.

Johnny had let them borrow his video camera so they could tape all the sick things I had been made to do this weekend.

Sam asked Johnny if he wanted something to eat but Johnny said no that he was on his way to church but he wanted to stop by and see if he could get another blow job from me.

Sam laughed and said sure, then looked at me and said, see you get breakfast after all. They all laughed. As the other finished eating I had to follow Johnny into the living room where he plopped down into the recliner.

I had to kneel before him and unzip his pants. I reached in and freed his cock, it was already hard. 7 inches but thin around. By now I knew what was expected and leaned in and took his cock into my mouth.

As I sucked the head I though how clean his cock tasted. How nice Johnny smelled. I started working my mouth up and down the cock. I would occasionally squeeze Johnny's balls.

As I was bobbing my head up and down, Sam came in with the video camera and started video taping me yet again. Johnny was running his hands through my red wig.

I pulled off of Johnny's cock and started licking his balls and the hard shaft. He must have liked that because he was muttering "oh yea...oh man that is good" over and over again.

I went back to sucking on his cock. I would alternately suck on the head of his cock them bob my head up and down as I continued to squeeze his balls.

I could feel his cock start to get bigger and knew from experience that he was about to cum. Thank God he let me pull back some so I could swallow it all as he came.

When he had finished I licked around his cock and balls cleaning them of what cum I had missed. Johnny patted me on the head like a dog and said I did a real good job.

He told Sam bye and said he might come back this afternoon if it was ok. Sam told him he could come by any time. ____________________________________________________________

After breakfast, or after they ate breakfast I had to get on the scales and weigh again. I was down to 146 pounds. Just 6 more pounds and Sam would allow me to eat again. He eventually wanted me to weigh 130 pounds.

Sam made me do some stretching exercises while they watched. I also had to do some jumping jacks, some sit ups, and other exercises, as they watched and made fun of me.

Megan told Sam she was going shopping later and asked if he wanted to go. He declined but asked what she was going shopping for.

"It's not for me silly, I am taking Jasmine. She needs her own clothes plus she can't wear that same pair of heels all the time."

I panicked. "Please no I cant go ot dressed like a woman."

Sam was next to me and he slapped me hard across the face. "Shut up you stupid whore, you do what we say. Besides you went out Friday night."

I was rubbing my cheek trying not to cry again. "But that was just to the ATM machine, not many people saw me."

Megan was laughing and said not to worry we were not going to the mall or anything just to some thrift and second hand stores. There would not be to many customers in the stores on a Sunday.

I still did not like the idea but I really did not have a choice. I was still thinking about it when the phone rang. Sam grabbed it and checked the caller ID.

"Is that hot wife of yours, maybe I should answer it and talk to her. Or have Megan answer it and pretend to be some prostitute you brought home last night."

"No please....."

They were all but rolling in the floor laughing when he handed me the phone.

Tonya, my wife, was calling form Florida. She had taken the kids and her parents and went on vacation and would not be back until next Sunday.

She was still very upset with me, She did not like that I had to cancel at the last minute because of work. She did not talk long, I think she just called me to tell me how much fun they were having without me.

I was really depressed when I hung up the phone. Megan told me not to worry, shopping was just what I needed to cheer me up.

Megan told me to go take a nice long hot bubble bath. Then shave my legs and underarms. She would be in to inspect my work later.

After soaking in the tub and letting my mind just drift and not think about what has happened to me or worry about what might happen to me, I got out of the tub and found my wife's razor.

I shaved my legs as best as I could. The bathroom door opened and it was Megan coming to check on me. She actually told me I did a good job on my legs, but I needed to shave all the hair off my pubic region.

It was humiliating because I had to shave in front of her but I shave the hair around my cock and balls off like I was told.

Megan had laid out an outfit for me to wear. It was a pretty yellow sun dress with a v-neck and came to just below the knee. She had also laid out a simple pair of white panties and a matching bra.

She told me she thought about making me wear pantyhose but it would be to much of a hassle to take them off when I tried on clothes. She did find me a pair sandals to wear instead of those painful black heels I had been wearing.

She then made me paint my fingernails and toe nails a bright pink. She did a great job on my makeup and applied a coat of dark red lipstick and then some gloss to my lips.

When I went down the stairs Sam and Steve both just stared, Sam finally spoke up and told me that I looked like a hot soccer Mom, not the whore I really was inside.

Sam made me give him my password to my Internet account, he said he had some things to do while we were gone shopping. I also had to give him a credit card.

As Megan, Steve and I left, Steve was driving my Lexus. Megan was telling Steve that we had to go by the ATM machine again because most of the stores we were going to did not accept credit cards.

After I withdrew $700 with my debit card, Megan Told Steve, now all we have to do is pick up Lori who is her best friend. Steve asked why did she have to go and Megan said no one can find a bargain like her, besides the more the merrier.

We got to Lori's house and Megan ran in and told her to get a move on. When they returned, Megan told Steve that she wanted Lori to drive, she needed the practice for her drivers test next week. I tried to protest but to no avail.

Lori was a hot little redhead, green eyes, small cute breasts and a pert butt.

Steve crawled into the backseat with me and Lori started to pull out in traffic. She was not doing bad but she was scared and going slow. Megan told her to give it some gas and Lori floored it. I thought great, All I need is for us to get pulled over.

I was letting an underage girl with no license drive my car and I was in the back seat dressed as a woman. I did not need to go to jail dressed like this. ____________________________________________________________

We made it to the first store without incident. Steve stayed in the car as Megan and Lori led me into the store. I was nervous but after everything that had happened already this weekend, Shopping seemed pretty tamed.

The girls led me from one rack of clothes to the next one, holding things up trying to decide what would fit and what would not. I noticed most of what they chose would be tight, short and look slutty on me.

Especially this one pink outfit. It was a very short lycra skirt and a small pink tube top. They also picked a short black party dress, a white see through blouse, a shirt denim skirt and a black skirt with pleats. Megan had also picked out some gaudy bracelets and clip on ear rings.

I had to go into the dressing room and try each outfit on. Megan made me come out each time and let them see how the clothes looked on me.

When I came out wearing the pink outfit, there was a guy waiting for his wife who was in the other dressing room trying something on. He was still leering when his wife came out and caught him looking at me.

She was not pleased. I figured she was mad at him but she turned on me and she called me a dirty slut and said I should stop prancing around in front of her poor husband or she would bring me down a notch. I quickly went back into the dressing room stall to get away from her.

I was carrying three bags of clothes as we went back to the car. We went to the next thrift store and repeated the process. At the second store Megan also bought me a workout leotard and some exercise videos. One was a workout tape that concentrated on the butt muscles.

At the third stop Megan told me to stay in the car with Steve. I noticed it was a costume store. I wondered what they were going to buy in there.

As we were sitting in the car Steve started looking through the bags. When he came to the pink outfit he took it out of the bag. He had a wild look in his eyes when he told me to put it on.

"Please I do not have anywhere to change clothes."

Steve told me to do here in the car. I did not have a choice so I stripped off my yellow dress and took the pink skirt and shimmied into it. Then I put on the tube top.

Steve told me I looked ridiculous with the bra on under the tube top and ordered me to take my bra off. As I fixed the top back in place Steve told me I looked like a cheap hooker and that we all know what hookers do in the back seat of a car.

He was unzipping his jeans and fishing out his already hard cock. I looked around to see if anyone could see what I was about to do. The parking lot was mostly deserted, only two other cars in the lot.

I took a deep breath and leaned down, I knew it was dangerous doing this here so I wanted to get it over with as quick as possible. Since his cock was already hard I skipped the preliminaries and took the entire length into my mouth.

I felt the tip of his 7 1/2 inch cock hit the back of my throat as i started bobbing my head up and down. I was sucking hard. I pulled back and was sucking just the head as I worked my hand up and down the shaft.

I heard Steve mumble something about me getting better at sucking cock. I continued to suck and to jack him off.

"Oh My God Megan, I can't believe he is doing that to Steve. Does that not bother you?"

I started to lift my mouth off of Steve's cock but he held my head in place as I heard Megan reply to Lori. "No I don't mind, at least I do not have to do it now and Steve says she's good at it. I just wish they had waited so I could video tape it." They both laughed as they got in the car and shut the doors. Megan grabbed the camera and started taping.

"Look She is wearing the pink outfit you got her."

I know I was blushing but no one noticed because of the cock in my mouth. After several minutes all of my effort paid off as Steve came hard, flooding my mouth.

I had no choice but to swallow all of his cum. When his cock started going soft he let my pull back and his cock slipped from my mouth.

Megan handed me a Kleenex to wipe the cum from my face. She was laughing because she said I must be good because I could do that and not mess up my lipstick.

Megan then told me what they purchased in the last store. They had bought me two new wigs. A long blonde wig and a short red one in what is called a page boy cut.

She said they also got me a special outfit but it was a surprise and I would see it later. She also told me we had just two more stops to make.

The next stop was at a small lingerie shop. I asked if I could change back into the yellow dress but they all said no. So I climbed out of the back seat trying not to let my skirt ride up to far.

Even Steve was going into the lingerie store. Both sales women were staring at me as we looked around. I had to purchase 3 garter belts one in pink, one in black, and one in white.

They chose several bra and panties sets for me to buy. Then several pairs of stockings. The sales staff may have been looking at us strangely when we entered but when they seen just how much stuff we were buying they could not wait to help us out.

As we were putting the bags in the trunk Megan announced that we had just one more stop to make. We were going to the shoe store. It was a shoe store close to campus and Steve said one of his room mates worked there.

As Megan, Lori and I went to the women's section Steve went to talk to his friend. Steve's friend was named Bill, he was 6' tall, 190 pounds and black. Bill not only worked there he was the weekend manager.

Megan made me try on several pairs of heels. One pair was knee high boots that zipped up and had a 5 inch pencil thin heel. It was all I could do to get them zipped up and Megan had me walk back and forth.

There was no other customers in the store since it was late Sunday evening and almost closing time. We went to the register for Bill to add up how much it all cost.

Megan said we did not have any money left and asked if maybe we could work something out and winked at Bill. Bill laughed and asked her if Steve had not told her he was gay.

That was when Steve told Bill I was a guy in drag. Bill did not believe him at first. Steve had me pull up my skirt and pull my panties to the side to show Bill my limp cock.

Bill was laughing hard and asked Steve where they had found me. Steve told him the whole story and even said he would let him see the video tapes they have made of me.

Finally Bill said maybe we could work something out after all and went to the front to locked the door and put out the closed sign. Steve told him to wait and ran to get the camera out of the car.

When Steve returned with he camera, Bill made me take off all my clothes, he even made me take off my wig. Bill explained that he liked real men but a sissy man would do for now.

I had to follow Bill into the back and he ordered me to my knees. I had to suck and lick his 7 inch black cock until it got hard then he turned around and I was ordered to kiss his ass.

I had to kiss each cheek then he ordered me to lick between his but cheeks. It was humiliating. He spread his cheeks and ordered me to rim his ass.

I had never done anything like this before so I stuck my tongue deep into his ass. I swirled my tongue around rimming Bill's ass.

He seemed to like what I was doing as he was pushing his ass back to meet my tongue. Bill finally pulled away and turned around again. He told me to get his cock all nice and wet because it was the only lube he was going to use.

I was slurping on his cock trying to coat it with spit. He pulled his cock out of my mouth and walked around behind me. I felt him spread my ass cheeks and start to push his cock into my ass.

I noticed Megan was staring in awe as Steve was looking on video taping everything. Lori looked all glassy eyed, I do not think she had even seen so much perversion in her life, let alone in one day.

I felt the big head of Bill's cock pop into me. He waited a minute then started working his cock in and out going deeper each time. Bill kept fucking me for almost 30 minutes, he said I was tight and he did not want it to end.

Soon though Bill pushed deep and I felt his cock throb right before he came inside my ass. By the time he pulled out I had cum running down my thighs.

Megan thanked him for the shoes and told him I would be back in the future and it was up to him how I made my payments. Steve threw me my panties and told me to wipe the cum off of my legs.

He then told me to put my panties back on as he picked up my top and skirt. I had to walk to the car wearing only white lace panties and boots, the heels were so high I had to take very small steps to keep from tripping. ____________________________________________________________

When we returned home I was not allowed to dress as they made me carry each bag in one at a time. I do not know how many trips I made back and forth but I was glad that no one drove by and seen me in just panties and boots.

After I had brought in all of the stuff from the car, I was allowed to go to the bathroom and clean up. Reapply my makeup and put on my new blonde wig.

I was told to put on a fashion show. I modeled all of my tops and skirts, then the dresses. The final outfit was the pink skirt and tube top, Sam had not seen me in it yet.

I was to wear my pink garter belt, pink stockings, a lacy pink pair of panties and my boots. When I walked out Sam said I looked like a go-go dancer.

They decided to make me dance for them. I had no idea how to dance so I just kind of shimmied around shaking my ass for them.

Lori was on the cheerleading squad and dance team at school so she got up and showed me some moves. I tried to do what she showed me but I was still a little stiff and the boots were hurting my feet.

After they had there laughs Steve took Megan and Lori and left, leaving me alone with Sam. He mad me dance some more.

Then he made me go change into my tight yellow leotard and do an more exercises for an hour.

I was starving and exhausted by the time I was done.

i was allowed to take a shower and then I had to put on one of the new teddies that Megan had bought for me. It was light blue with garters and a snap crotch. I slide the stocking up my legs as Sam watched.

He sat on the bed and had me kneel before him. I knew what to do so I took out his cock and started kissing and licking it for him. I knew from experience that Sam really liked to have the head of his cock sucked.

I was sucking the head of his cock and squeezing and messaging his balls. I was working my head up and down Sam's cock and was soon rewarded with yet another mouth full of cum.

When Sam had pulled up his pants he said it was time for bed. He took the cum encrusted white lace panties I had worn on our shopping trip and shoved them into my mouth. he took a stocking and gagged me like last night, Then he blindfolded me again.

This time he made me lay face down on the bed. Sam had brought some rope from his house and tonight he tied both hands and feet to bed.

As he turned out the lights he told me he would be over early in the morning to untie me and supervise what I was to wear to work the next day. ___________________________________________________________

Again, I would appreciate any and all feedback. Should Jasmine have further adventures? Let me know. Thanks.

Next: Chapter 4


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