Cross Dressing Sissy Slut Transformed Into Shemale By Dominant Strap On Lesbian.

A young cross dressing sissy is forced and transformed into a shemale by the mature and dominant hands of two strap on dido yielding lesbians. Written by Donna for kinkysexstories.org

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My name is Donna and I have been bi-sexual ever since I was old enough to have interest in sex. I realized early in my life that I have a dominant personality and I also learned what turns me on most is to take something beautiful and submissive and transform them into my personal toy. I still recall my very first boyfriend. He was a jock and very masculine and I liked him a lot. When we were making out, my instincts told me to wrestle him to the ground and force myself on him. It got me so hot that I had to go further and I tied him up and then put make up on him and then a bra and panties. Then I fingered his asshole until he came. After a year of dating him, I had transformed him into a flaming homosexual and I still masturbate about doing so today.

These days, I am mostly a lesbian and prefer to fuck women. But sometimes I spot a sweet young and innocent boy and bring him into my lesbian affairs and eventually transform the sweet little sissy into a gay twink boy. But if I really like him, and his transformation makes me really hot, I try to go all the way and transform him into a shemale, getting him breast implants and if I am lucky, he becomes a sweet bride to a massive stud.

I am 42 years old and my girlfriend Misty is 22. We like to go out to bars and wait for men to hit on us, and then shoot them down so badly that they cry. It’s a little game we play sometimes. One night we were out and a very young and sweet boy began to hit on Misty. She toyed with him for awhile and we both could tell he was very submissive, just the way we like it. While at the bar, he allowed Misty to apply some lipstick on him. That’s the test we give a boy. If he passes it, he comes home with us and we give him a night he never forgets.

Well Timmy agreed to come home with us and while driving him home, I put more lipstick on him and put two fingers in his mouth and told him to suck. He was a natural and my pussy got so wet. It was then that I knew Timmy was special.

“I think we have a little sissy boy here Misty.” I said to my girlfriend. “Look at how eager he is to suck. We won’t have to do too much work to transform him. He’s already half way there. Timmy, are you sure you aren’t gay?” I asked.

“No. I’m not gay.” He said.

“Well, I bet you have tried on a pair of women’s panties before haven’t you? It’s ok to tell us. We enjoy and appreciate that in a young man. In fact, it really turns us on. You want to turn us on now don’t you?” I teased him.

“Well, I do have a pair of my ex girlfriends panties that sometimes I put on.” He admitted as he blushed.

“And have you ever had a man’s cock in your mouth sweetie?” I teased.

“No, of course not. I’m not gay.” He said.

“Well, there’s nothing wrong with it. And there’s nothing wrong with being gay. Misty and I are gay, but we like boys too. Especially cute boys who wear panties sometimes. ” I said and held him close to my chest until we got home.

Misty and I undressed Timmy in front of the mirror and began to caress and nurture his sweet and sexy little sissy body. It was already very feminine with almost no body hair or muscles. Misty kissed him as I stroked his little sissy cock until it was hard.

“Your cock is not very big sweetie, ” I whispered in his ear, “but your ass is a work of art. Most women would kill to have an ass like yours. ” I said as I played with his butt cheeks like puddy.

“Now Misty is going to apply some make up to you while I put these panties on you and you can show us how much you like to wear them. ” I said. Timmy said nothing and let us completely play with him. My pussy was soaked already watching this young sissy submit to us. He had no clue what he had gotten into.

Timmy’s mouth looked fantastic with the heavy red lipstick and I picked out a bra for him and placed it onto his soft and barren chest. I looked down and saw his tiny penis sticking out of his panties and gave it a little tug.

“Looks like somebody likes all this attention. Your little girly clit is very excited isn’t it?” I asked.

“YEs.” He said whimpering.

“Don’t be scared Timmy. You are very lucky to have found us. We are going to bring you to heights of pleasure you never even dreamed of. Now lift up your foot so I can put this stocking on you.” I instructed him.

After Misty and I had cross dressed Timmy into a beautiful little sissy slut, we paraded him around our place and teased him and tickled him and tortured him.

“Timmy, you are absolutely beautiful. All of our lesbian friends would love to have a sweet sexy girl like you. Don’t you feel beautiful? Your lips look fabulous. Don’t you feel so soft and feminine? Like a ripe blossom that needs to be plucked. Doesn’t it feel wonderful to let go of all your masculinity and allow yourself to be free and beautiful? Now it’s time for your reward for letting us dress you up and sissfy you” I said.

I took Timmy by his soft and feminine hand and led him to the bed. I lay him on top of me and could feel his small erect cock sticking out of his panty and rubbing against my stocking. I could smell the slutty purfume we sprayed on his neck. My pussy was drenched in wetness now and I longed to feel his sissy prick inside me.

I grabbed the sissy’s ass cheeks and plunged his dick into my pussy. Ahhhh. I very gently and softly rocked his hips back and forth into my pussy. Slow enough that he wouldn’t cum.

“Now this is the way you should fuck a woman.” I said. “Soft and slow and gentle.” I reached behind him and stuck my finger deep into his ass and watched his eyes light up and his painted mouth open wide. “Now just relax and enjoy it.” I said.

Meanwhile my girlfriend Misty had straped on a large black strap on dildo. She had grabbed some anal lube as well and inserted her lubricated finger into his virgin ass hole right next to mine. Timmy moaned and squirmed and struggled as I held his sissy arms tightly.

“Very good sissy boy. You can take 2 fingers up there. That’s what we like to see. Now just relax and don’t cum yet.” I said.

Misty put the head of the large black strap on cock against Timmy’s ass cheeks as he continued to sweetly move in and out of my pussy.

“Now Timmy look at me. I want to see your face as you get fucked for the first time.” I said and laughed at him. Misty slowly inserted the massive black cock into his virgin ass and because it was so tight, his entire body began to shudder and shake. “Just relax Timmy and keep fucking me. You are doing a very good job.

“It hurts.” He whimpered.

“I know it does sweety. But it feels good too doesn’t it? It’s ok. You can tell me. I won’t tell anyone. ” I said.

“Yes, it feels good too.” He admitted.

“Well don’t cum just yet. Let Misty fuck you and take it like a man. She can fuck you better than you can fuck me I bet.” I said laughing.

Every time Misty thrust into Timmy’s ass, his little dick thrust into my pussy. I began to cum and climax as I watched the look on Timmy’s face as he took it in the ass for the very first time. His painted face looked so sexy as he allowed Misty to violate him. He was so tight that even the smalest of movement of the strap on caused all of his skin to move. It was so tight and so sexy to watch.

“Now do you feel your ass pussy begin to stretch and welcom the big cock?” I asked.

“mmmmmmmm”, was all Timmy could say.

Misty and I began to feel his little sissy ass muscles tighten up and we knew he was about to cum.

“Looks like you are starting to enjoy this my little sissy slut. But don’t come just yet, we have much more for you.” I said. But just then Timmy’s ass cheeks gripped down on the large cock that was violating him and I had to take him out of my pussy before he exploded. “My sweet little Timmy. I knew you were going to enjoy that. You did a very good job for your first time. I am proud of you.” I said.

Timmy was shaken, embarrassed, and stipped of all his dignity. We had broken him and he was confused by the pleasure of it.

Misty and I undressed Timmy and gave him a hot bath. We shaved his pubic hair and his other body hair and he let us. He was loving all the attention. We then dried him off and dressed him in a frilly teddy negligee. We told him that from now on, he must wear our panties at all times.

We brought Timmy into our bed that night and he slept between us as we stroked, fondled, and fingered him. The next morning we tied him up and took turns fucking him with an even bigger strap on, stretching his sissy ass pussy to accept our cocks easily . This time we had to put a cock ring on small penis to keep from coming. Timmy was starting to enjoy being fucked in the ass as much as we enjoyed fucking him.

We made a deal with Timmy that if he wanted to be part of our love triangle, he had to be dressed up as a woman when he came over. Since poor Timmy couldn’t seem to get sex anywhere else, he agreed. We took Timmy shopping and bought him clothes. And when he came over to see us, he came over dressed in these sexy and often slutty clothes. It was a thrill to see him so nervous and scared at the door, and then to take him inside and have our way with him. We had almost completely transformed him into a shemale and he was totally unaware.

One day I told Timmy that Misty and I wanted to take him out to a bar dressed like a woman. Timmy didn’t like the idea at first, but we he was so whipped, that we knew we could get him to do anything we wanted. We dressed him in a wig and a sexy red top with black gloves to cover his arm hair and hands. He looked fantastic.

“Are you ready for your big night out on the town with the girls?” I asked.

“”Yes but I am very nervous.” He siad.

“Oh don’t be. You look great. I think it’s about time the whole world saw how sexy we have made you. We want to show you off Timmy.” I said.

We took our little sissy slut boy toy out to a gay bar. He was the new bitch on the block and all the gay bears were making eye contact with our new little sissy.

“Now Timmy, I think it’s about time we found you a boyfriend. After all, Misty and I can’t fuck you all the time. ” I explained.

“No, please. I don’t want to be with anyone else. I love you guys. Please don’t make me be with a man.” He begged us.

“Stop bitching. We will keep fucking you in your little sissy ass until we can find you a real man that you like ok?” I said.

“Well, I guess so.” Timmy said crying.

Just then as massive muscle stud approached Timmy and asked to buy him a drink. We nodded yes and we all talked awhile.

“Why don’t you and this stud go dance a little while. Now Timmy, I want you do do whatever he wants ok?” I said sending Timmy away. Misty and I watched as our submissive sissy held his frist real man close and creamed our panties as he was fondled and then kissed for the first time.

As the bar closed we asked the stud to come home with us and he agreed. He was a gorgeous masculine man and he held Timmy in the back seat sneaking his hands into Timmys panties as the two kissed in silence.

Back at our place, Timmy was getting turned on by this aggressive gay bear and it took no coaching from us to get him to suck his cock. In fact it was Timmy who went for it first. Placing the huge shaft into his sissy virgin mouth and sucking like a pro. Timmy cupped his giant ball sack and we watched as his painted lips sucked up and down until the gay stud began to convulse and exploded all over Timmy’s sissy face.

“Very good Timmy. We have taught you well. Now that wasn’t so bad now was it?” We said as we applauded his first blow job. After the stud had emptied his cum all over our sweet little sissy’s face, he went home and we took Timmy to bed and fucked his ass good and hard.

Misty and I asked Timmy to move in with us and told him that if he did, he must be dressed in drag as often as possible. To our surprise, Timmy agreed and after a few months, Timmy was dressing as a woman full time. We took pleasure in making him as feminine as possible and stripping away any sense of masculinity he once had. We stopped letting him fuck us and now, we only fucked him with strap ons. But of course we made him perform oral sex for us sometimes twice a day.

We took Timmy out shopping dressed as a woman, we took him out to eat dressed as a woman, and slowly, Timmy stopped wearing his boy clothes altogether. We even had all our lesbian friends over and allowed them to take turns dressing up our boy toy and then fucking him. But one lesbian friend tried to use am extra large steel dildo on Timmy that stretched our his ass pussy so far, it took weeks for it to shrink, so we had to stop the parties.

One night, we tied Timmy up and teased him with his favorite strap on dildo.

“You want this cock don’t you, you little sissy.” I said.

“Yes, you know I do.” He begged me.

“Timmy, I know what else you want. Even if you don’t know you want it yet. You want to be a woman. You want to have breasts and be our little shemale sissy slut don’t you? You want to do whatever it takes to please us. It’s your nature. It’s what you were born to do. ” I said.

Timmy began to cry and sob. “I don’t want to lose you and Misty. But I don’t want to have tits either.” He cried.

“Now deep down you have always wanted this. To be a real woman, to be our special little toy. To serve and please us forever. Timmy you will make us very happy by doing this. We can no longer continue to fuck you unless you take the next step. It’s time you got breasts and became a real woman for us.” I said.

Timmy cried uncontrollably and I held him in my arms and kissed him untill he calmed down and said, “ok, I will do it.”

I squeezed him tightly and placed my black dildo into his mouth to suck which stopped his sobbing. The next day Misty and I took him in for his breast implants. When we picked him up, he was gorgeous. Almost as sexy as Misty. Poor Timmy was crying and his mascara was running all over his pretty white blouse.

“Timmy, you look wonderful. Don’t be sad. This is your first day as a real woman. Lets get you home and break you in. Misty and I have bought a whole set of new bras for you. But from now on, we are going to have to call you Tina.”

Our sissy slut Timmy, who was now Tina, began to really take to his forced womanhood. In fact, he was much happier with breasts and was definitely much sexier. His transformation had been complete. Misty and I were so pleased how we transformed our sweet sissy slut Timmy into a gorgeous submissive shemale, that we couldn’t keep it to ourselves. I began to seek out gay play mates for our new shemale Tina.

I took a picture of Tina and placed an ad in the online personals.

“Newly transformed shemale looking for studs to suck and fuck for free.”

The answers poured in. I was very selective and finally choose a very tall and muscular older gay man to be Tina’s first. When he arrived at the door I told Tina to hug him and let him kiss her. Well once they started to kiss, there was no stopping the raw sexual power of those two. The stud picked up our shemale and placed her gently on the couch with her legs in the air and quickly tore off her panties and thrust his massive cock into Tina’s ass. Misty and I got naked and began to suck each others pussy as we watched Tina get man handled. Soon Misty and I began to orgasm. Then Tina began to cum in her panties but the stud was far from done and continued to put Tina in every position he could think of. Misty and I watched Tina’s limp tiny penis get bounced around as the giant cock when in and out until finally, cum spewed out of Tina’s ass pussy and ran down her crack.

Tina turned to us and said, “Oh my god, you have made me so gay. I just love cock in my ass” I came in my panties instantly.

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Misty and I began to set up more play dates for our shemale Tina. We began to even charge money for men to spend time with her. Fat men, old men, gay men, straight men, big men, small men, all men. Tina began to become a pro and took it all. Deep in her sweet submissive pussy ass.

Now Misty and I are looking for a new sissy slut to transform into a shemale.

Are you man enough for two dominant stap on lesbians?

Sissy slut transformed into shemale by dominant strap on lesbians sex story.