Kinky Sex Stories

Forced Sissy Slut For Girlfriend’s Mom Sex Story

Written by Sherry Wilson

My daughter was dating a very cute young 18 year old boy during her senior year in high school. He was very sweet and extremely good-looking. I was recently divorced at the time and found myself constantly fantasizing about him and making him my love slave. But of course he was my daughter’s boyfriend. He had very feminine traits and I would try to impose that he was gay and that my daughter should find a real man. But secretly I did this only in hopes that they would break up, and I could have him.

Amanda, my daughter, was a very voluptuous young woman. Her breasts had developed to a very large size at an early age and she always attracted all the shy and sweet boys in her class. She was built like her father. Big boned and she even had a very dominate personality. She would bring the boys over and seduce them, turning many young virgins into non-virgins and thus making her very popular. She always threw parties at our house and there was a steady stream of young boys around.

Amanda had chose Brandon as one of her favorites, as he was mine too. I would listen to them in her bedroom as my daughter easily took control of him and seduced him into her bed. Brandon was so sexual, he was so beautiful for a man, and seemed to have such amazing female mannerisms, that you could not resist wanting to make him your lover. At least I couldn’t.

I had a plan to steal my daughter’s boyfriend away from her. I kept telling her that I was sure he was gay and gave her some ideas to find out for sure. I began to buy Amanda sexy lingerie, and I instructed her to begin to model it for Brandon after school in her room. She did so and I listened through the door of her bedroom.

Amanda would make Brandon dress her up in her sluttly outfits, and he learned how to apply her makeup on, what perfume to apply, and how to put on stockings. Once dressed, Amanda would tease Brandon until eventually they would have sex.

Then Amanda began dressing up Brandon in her sexy slutty lingerie and you could tell by the tone of his voice that he loved it. He would apply makeup and sometimes they would go shopping for him and buy him girly clothers. I suggested to my daughter that she begin to make him look at porn of naked men from Playgirl with her before they had sex. She said Brandon would do anything for her and he seemed to even talking about how sexy the studs were.

One day after school while Amanda was dressing up Brandon into his sissy slut clothes, I opened the door to the bedroom and caught him.

“Well, don’t you make a beautiful woman!” I told Brandon.

He blushed and said, “Umm, Miss Creegar, you caught me. I feel a little silly right now. Please don’t tell anyone you saw me like this ok?”

“Don’t worry, I think you look fantastic. Amanda has done a wonderful job with you. Any man would be lucky to have you. “I said and laughed at him.

“Thank you Miss Creegar, but please don’t tell anyone.” He begged.

“Amanda, can I help you to make Brandon even more beautiful?” I asked.

“Sure mom, I still have not finished with his hair and makeup yet. But don’t you think he has great legs?” My daughter asked.

I stood behind Brandon facing the mirror and began to add pig tails to his hair and applied red lipstick to his full lips. I put too much mascara on him and he reall did look like a first class hooker. He was suck a beautiful man. I told him how to hold his wrists, limp. And both Amanda and I walked him around the room letting him get used to his high heels. He seemed to completely enjoy all the attention and played the role like a pro. My pussy was so wet. All I could think about was taking him up to my room and watching him suck my 1o inch black dildo.

“I’ll leave you too alone now, but Brandon honey, you look fantastic and if you ever want to go shopping with me, I would be thrilled to take you.” I said.

“Thanks Miss Creegar.” Brandon said sheepishly.

I listened through the door as Brandon the sissy slut fucked my daughter. He was so submissive in the way he fucked her. Asking her to put his cock in when he was ready and making sure she came as many times as she wanted before allowing him to cum. When she was ready, she inserted a small dildo into his virgin ass and he came instantly. She was training him well for me and neither of them knew it.

One day Brandon came over the house when Amanda wasn’t home. I offered him some wine and told him that I needed to go shopping and wanted him to join me. I took him to Victoria’s secret picked out a few outfits for me and made him wait while I tried them on. Then called him into the dressing room to tell me how I looked.

“Brandon, since my daughters birthday is coming up, why don’t we buy something nice for you to wear for her. You know how much she likes to see you in lace and panties.” I said.

I picked out some white lace panties, a white satin bra, a mini skirt, some pink stockings and a teddy. I forced him into the dressing room with me and I stripped him down.

He was not a very well endowed young boy but he did have a very sexy body. He also had a fantastic butt that I could not keep my eyes off. I slipped Brandon into his sissy clothes, spun him around, felt him up and down, and got him very horny.

“What do you think Brandon? Do you think Amanda will like you in this?” I asked.

“Very much.” He said.

We went home and I dressed him up again in my bedroom putting on lots of makeup and giving him some red high heel shoes to wear. I told him that Amanda would be home shortly and we would surprise her for her birthday.

I took out some porn of naked men and told him to read this while he was waiting and locked him in my room. Just then Amanda called and told me she was going to be home very late because she had gone over to a boys house that she had just met. I told her to take her time and enjoy herself with her new guy.

I left Brandon alone in my room for a while looking at pictures of hung and muscular naked me. When I returned I asked him which one he liked the most. He blushed deep red and pointed out a very strong and extremely hung man dressed in a lumberjacks uniform. He giggled as I stroked his long hair and began to message his neck.

“Would you like to watch a movie while you wait?” I said.

“Sure. Thank you.” Brandon said.

I picked out a prono movie about a woman dressing up a man in sissy clothing and then turning him into a neighborhood slut. It was one of my favorites. I lay next to Brandon stroking his pink stocking thighs and making sure his penis became very erect while watching the movie. He became so horny he began to squirm and moan softly.

“You like this movie don’t you sweetie?” I asked.

“Yes, I do. But I don’t think I should.” He said.

“It’s ok my sweet sweet boy. You should not be ashamed of being excited. I love that you like this movie because it excites me also.” I said.

I took him and began to kiss him. He tried to resist at first but soon began to kiss me back. He kissed so sweetly and gently. I began to stroke his cock in his white lace panties.

I stopped and asked him to go to my dresser drawer and take out what was in there. Brandon got up and walked in his high heels, making his ass look just like a woman’s. He took out the 3 dildos I had in my drawer and brought them over.

“Now which one do you like the most?” I asked.

Brandon chose the largest dildo. It was black and shaped exactly like a perfect cock with balls.

I gave it to him to hold while I picked up the strap on dildo.

“Now do exactly what I do!” I said.

I began to suck the dildo and watch as Brandon repeated my moves. He was able to take it only half way down his small throat. Just like a young virgin would. I almost came in my panties just watching him. You could swear he was a girl.

“Very good Brandon. From now on I am going to call you Brandy ok?” I said.

“I don’t know Miss Creegar, I am starting to feel a little uncomfortable. I don’t want to upset your daughter.” He said.

I told Brandon that if he did not do exactly as I said, I would tell all his friends that he liked to dress as a girl. And I also told him that Amanda had been having sex with other boys for a long time, and was just using him to play with him. Brandon began to cry and sob. I held him in my arms and forced the dildo back into his small pretty mouth. This stopped his crying. I then slid my finger into his ass and he began to moan and squirm in my arms.

“See Brandon. You are in good hands. I am going to make you much happier than my daughter ever could. I have wanted you to be my lover since I met you.” I said and kissed him deeply and I fingered his ass.

“It’s going to be fine.” I said. “Are you horny?”

“Yes, I am very horny.”

“Are you willing to do anything I ask?” I said.

“Yes ma’am. I will do anything you ask. Just don’t tell anyone ok?” He begged me.

I told Brandon to practice sucking on his favorite dildo and I left the room and called 2 of my neighbors, whom were gay and would love to have a go at this fresh young sissy slut. I told them they would have to pay me $200 each. I explained that Brandon was 18 and was a virgin and had never had sex with a man. I told them to come over immediately.

When John And Dave arrived I told them to wait as I went into my bedroom and found Brandon sucking on his favorite black dildo. I handcuffed Brandon and put a chastity belt around his small penis. I told him that I had a surprise for him. I explained that before I would fuck him, he had to do me a favor. And if he did me this favor, I would be very good to him from now on. But he had to prove he was worthy. He was so horny that he was more than happy to do anything I asked.

I got up and let John and Dave in the room. Brandon looked a little nervous and I reassured him that everything would be ok and that he would enjoy this very much.

John and Dave took off their pants and lay down next to Brandon on the bed. John forced his cock into Brandon’s mouth while Dave began to lubricate his ass. Brandon looked very nervous as he began to suck the giant cock and he seemed even more concerned about the huge dick being worked into his ass.

I sat on the chair and began to fuck myself with the black dildo Brandon had been sucking earlier. Brandon was whimpering as he began to be rammed from being. I must admit that John and Dave were being very gentle with this virgin sissy slut and soon Brandon began to relax a little.

John came first into Brandon’s mouth and I instructed him to suck it all down like the good little sissy that he was now. He swallowed all the cum and then John began to kiss Brandon as Dave continued to try and get his entire cock inside of Bandon’s ass. Soon Dave pulled out and began to spew come all over Brandon’s bra.

When the boys were done with my sissy, they got up and walked out of the room and left $400 plus a tip on the kitchen table.

I held Brandon in my arms as he cried and whimpered a little bit and then took off the chastity belt on his small penis. I then told him he had done very well and that from now on, I would take very good care of him.

I placed Brandon on top of me and took his penis and slid it into my soaked pussy. I grabbed his delicious butt and began to move him in and out of my pussy at the rhythm that I liked best. I came and came all over his small dick as I thought about what had just happened. I kissed him and then inserted 2 fingers in his ass and he came all over my stomach.

Brandon, you may not realize this but you one very lucky little sissy.

“I love you so much Miss Creegar. I only want to make you happy.” Brandon said softly.

“That’s a very good sissy slut. Now go to sleep and get your rest because tomorrow there will be more visitors.” I said.