Kinky Sex Stories

Sex Story Of Forced Feminization With Older Woman Helps A Sissy Come Out Of The Closet.

This sex story of forced feminization with an older woman tells the tale of how a sissy city boy moves to the country and is helped to come out of the closet.

I lived in LA for many years and grew tired of the chaos and craziness that surrounded me. It was always a dream of mine in my twenties to move to the country and live the good life. On my 30^th birthday, I made my dream come true and moved to Northern California and found a country home to rent by a mountain lake. I had no idea then, that I would get so much more from my country home than natural beauty. I would get the sexual bliss of my life and discover things about me I had never known.

When I began looking for a place to live, I stumbled upon the perfect country home on many acres that faced a mountain lake. I contacted the landlady named Barbara and met with her. She and her husband owned the property and rented out the guest home that I would live in. The fist time I met her, I was immediately attracted to her, and I got a sense she was also attracted to me. She was a voluptuous older woman with blond hair, large breast, and hips that wouldn’t quite. She was warm and friendly and very nurturing and we hit it off.

“So a good looking young man like your self must have a lover or 2 back in LA.” Barbara said.

“No.” I said. “I am all alone now and starting over.”

“Well, you will find the men here very macho and strong and should have no trouble meeting someone.” She said.

“Do you think I am gay?” I asked.

“Well, I suspected you might be. You are a kind and gentle young man and around here, those boys are usually found with other boys.” She explained.

“I’m not gay. I’m just from the city, and not used to the outdoors and being rugged.” I said.

“It’s very refreshing to meet someone like you Sean, you seem sweet and you listen very well. That is rare around these parts. I will rent you the guest house, and I hope that we can become good friends. If there is anything you need, do not hesitate to stop by ok?” She said.

I moved into the guest house and Barbara and I spent lots of time together, taking long drives in the country side, shopping for furniture for me, and getting to know each other. I was grateful for her friendship and felt very comfortable with her. She was a very sensual older woman and I could not deny my attraction to her. Her husband William was a very macho man, very strong and built with a mustache and about twice my size. I dared not to act on my feelings toward his wife.

When summer arrived, Barbara and I went swimming in the lake everyday. She would wear her white bikini that her large busty breast practically fell out of constantly. I wore my long swim trunks at first until they ripped one afternoon.

“Sean, it looks like you need a new pair of swim trunks. Lets go into the house and see if we can find you something.”

She took me by the hand and led me into her bedroom.

“Lets see what we can find for a good looking young man in here.” She said. “Now take off your trunks honey and let’s play dress up. And don’t be shy, I have seen it all before. Strip!”

I was shy, but was enjoying the attention so I slid down my bathing suit and revealed my naked body to her.

“Now turn around and let me look at you so I can get an idea of what would look best on you.” She told me.

I turned around and felt her eyes all over my bare bottom. It was turning me on a little and my penis began to swell and rise a little. She slapped my ass playfully and said, “you are a sweet bottom boy indeed.”

Barbara reached into the drawer and pulled out a yellow bikini bottom with tie strings on the side. “Yes, this will do nicely.” She said.

“That’s a girls bikini bottom. I can’t wear that.” I protested.

“Sweetie, it’s the only thing I have for you to wear. My husbands swim suit is too large for you. He has a gigantic cock and has stretched his suit out completely. You are a smaller size, more like my size, and this is going to work just fine for you. Now stop fussing and come over here and let me show you how to put this on.” She said.

She slipped the yellow bikini between my legs and raised it up to my dick. Then she laid me down on the bed and tied the strings on the side. It was turning me on so much, that I got an erection and the tip of my dick poked out of the bikini bottom.

“Looks like someone likes wearing my bikini after all. I knew you would. But honey, you can’t go outside with your little penis sticking out of your pretty panty. Tuck that thing between your legs now and let’s get back to the lake.” She said.

I covered up my swollen cock, completely humiliated and followed Barbara back outside. As we wadded in the lake, she would occasionally grab me and tighten my bikini bottom for me.

When we were done swimming, we went inside to make some snacks in the kitchen. Both of us in bikinis and laughing and having fun. Just then, her husband Robert came home and I became frightened that not only would he find me in a bikini bottom, but that he would see that I was having too much fun with his wife.

“Don’t worry Sean, he won’t mind. He likes you, just act natural.” She assured me.

Robert came into the kitchen and saw me standing near Barbara in her bikini bottom.

“Hello Sean.” He said. “You been swimming today?”

“Yes Robert, we have been in the lake all afternoon and my swimsuit broke so Barbara gave me this one.” I explained.

“It looks better on you. My wife is a fashion genius. You should let her dress you up more often. She has done wonders with me.” Robert said.

Barbara put her hand on my shoulder and said, “turn around and show Robert the back”.

I tuned around feeling very uncomfortable, yet excited at the same time. I was suddenly aware of Roberts eyes on my bottom and I bent over slightly to lift it up.

“Isn’t he such a sweet boy?” Barbara asked her husband.

“Well, you two have fun. I have to put in a shift at the fire department and won’t be home until late.” Robert went into the bedroom to get his uniform on and then left the house while Barbara and I ate our snacks in the kitchen.

“Barbara”, I said. “What did Robert mean about dressing me up?”

“Well for years I have been buying Robert clothes and trying to make him more presentable. Trouble is that I often make the mistake of buying him feminine clothes and he hates that. He is such a masculine man and I often forget that. I am a very nurturing woman and always wished I had a daughter to dress up and take shopping. Someone soft, sensitive, and sweet to play with. Someone like you Sean. Robert understands this and knows we have a special bond. He wants me to be happy.” Barbara said.

“Do you want to dress me up?” I asked.

“Yes, I want to dress you up very much. I want to help you get in touch with your softer, more feminine side. I can see in within you, and that it wants to come out and play. This is why we get along so well together. I know that you want me to dress you up like a doll, I have known that you have wanted this for a long time. And I want it too.” She said.

“I am scared Barbara. I am scared that I will like it too much and lose who I am.” I said.

“You can trust me not to hurt you Sean. If you don’t like it, you don’t have to do it. If you like it, then we will follow it to wherever it leads. You have nothing to lose, and everything to gain.” Barbara said.

She was right. It made sense. She got up and took me by the hand into her dressing room. She slowly untied my yellow bikini bottom and began to dress me up in her sexiest lingerie. One piece of soft feminine garment after another, until I was transformed into a strange and exciting new form. A feminine form that stared back at me in the mirror and said playful, attractive, and soft.

Barbara’s nurturing hands, and reassuring voice, helped me to feel comfortable in my stockings, and panties and stuffed bra. It was so liberating to not have to worry about being so masculine and in control. To completely surrender myself and my body to this wonderful older women.

“You look fabulous sweetie. Don’t you agree?” She said.

“I feel good Barbara. You did a wonderful job.” I said.

“I am glad you think so Sean. I have wanted to dress you up for some time. You may not be aware of this, but I think you might be bi-sexual and perhaps even gay.” She said.

“What do you mean Barbara? I’m not gay am I?” I said.

“I suspect you are in the closet about a few things and long to come out. There is really only one way to know if you are gay and that is to be with a man. Have you ever been with a man before? “She asked.

“No, I never have.” I said.

“Have you ever thought about being with a man?” She asked.

“Well, maybe. Sometimes. But not all the time.” I said.

“I think there is a good chance you are bi-sexual Sean. And there is nothing wrong with that. I love you for it and love being around you just the way you are. I think you look so pretty in my sexy clothes. How about we go to the computer and look at some pictures. And you tell me if it turns you on at all ok? “Barbara said.

Well, I was wearing woman’s clothes. And not just clothes, but sexy slutty stuff. And I loved it. It was true that I had thought about men from time to time, but thought that was normal. Barbara had me very confused and was starting to make me thing that I might be gay. I was all very confusing but exciting at the same time.

I sat on Barbara’s lap, as she surfed the internet and found pictures of naked men. She would ask me, “how about him? Do you find him sexy?” I would laugh and giggle and squirm in my silk panties. I played along and was honest about some of the men.

“You like the muscle studs don’t you sweetie? I do too. But I also like the twinkie boys. I want to dress them all up, just like you.”

We laughed, and she would tickle me, and I would squirm around in her wonderfully warm lap. She picked out one very hot and hung man and said, “would you kiss him?”

“Maybe” I said.

“Would you want to suck his cock?” She asked.

“Maybe” I said.

“Would you want him to take you, and have his way with you?” She asked.

“Perhaps” I said.

“You are a tease Sean. You know how men think. You must give them what they want or they get very upset. Now let’s try again.” She found a very hung stud and asked me, “Do you want to kiss him?”

“Yes” I said.

“Do you want to suck his cock?” She asked.

“Very much” I said.

“Good boy. Now we are getting somewhere”. She said. “Do you know how to suck a cock?”

“I am not sure Barbara, I have never done it before.” I confessed.

“Well, Sean, I am going to teach you.” She said.

Just then, Robert came through the door and found me sitting on Barbara’s lap, dressed as a slut, and looking at naked men. I was completely embarrassed.

“Looks like you two have been having fun.” He said.

“Honey, I think Robert is finally coming out of the closet. Stand up Sean and show Robert how sexy you look.” She told me.

I stood up very shyly. Barbara told me to turn around and I did, feeling the eyes of her husband crawl all over my body. So this was what it is like to be an object of desire. It was actually very exciting.

“Sean, go over to Robert and let him touch you.” Barbara said.

I cautiously went over to Robert and he began to run his masculine hands up and down my legs. He turned me over and put his crotch against my ass and I could feel his large cock against my butt. I began to get an erection and my penis popped out of my panties. Robert caressed my fake breasts and kissed my neck gently.

“Sean is unsure about his sexuality. He was telling me that he thought he might be gay but since he has never been with another man, he can’t be certain. He also has confessed that he wants to suck someone’s cock and needs to be taught how to do it. I can see by his hard on that he at least enjoys you touching him. That is a good sign. How would you feel about helping me to teach Sean how to give a blow job?”

Robert spun me around and looked into my eyes and said, “Sean, you look very sexy in my wife’s lingerie.” He took my hand and placed it on his cock. It was huge and twice the size of mine. I was totally turned on and could not hide it. “I would be happy to help Sean come out of the closet and learn how to please a real man.” Robert said.

Barbara unzipped Roberts pants and pulled down his underwear and revealed an 8 inch cock sticking straight up at me. She took the cock in one hand, and cupped his balls in the other and demonstrated to me how to do it. Then she placed my hand on his large ball sack, and my other hand on his huge penis, and she placed her mouth over the head and began to suck. I watched her for several minutes as Robert looked down on us and moaned in pleasure.

“It’s your turn sweetie.” Barbara said quietly to me. I placed the tip of his penis in my mouth and began to suck up and down. Using my tongue as she had shown me to lubricate his shaft. Robert moaned and took my hair in his hands and moved my head slowly to the rhythm that he enjoyed. Barbara was encouraging me all the while and whispering soft things in my ear.

“That’s very nice. Oh he likes that. You are such a sweet little sissy that wants to please so badly. You are very good at this. Doesn’t it feel wonderful to have such a large penis in your soft and sweet mouth? It’s ok to like it sweet Sean. It’s ok to have the feelings you do. Faster, a little faster, take it a little deeper now my sissy.” Barbara said.

I felt Robert’s balls tighten and his cock grow larger in my mouth. Then ropes of cum began to spew down my throat and Robert moaned and his muscles tightened. Barbara forced my head from coming of her husbands cock and told me to swallow every drop he gave to me. And I did.

Sex Story Of Forced Feminization With Older Woman Helps A Sissy Come Out Of The Closet by Ian Anderson.