Kinky Sex Stories

Sissy Fetish Sex Story written by Ian More

My name is Ian and I have a large sissy fetish. I am a straight man who loves to explore his feminine side by dressing up as a sissy in my spare time. Or better still, having a beautiful and strong women dress me up as a sissy. This fantasy turns me on more than anything else and I can’t get enough of it. I am writing this sex story in a white cotton body suit with little white bows and lace.

This is the true sex story of the first time I had the courage to tell a women of my sissy fetish.

I was on a business trip in Miami to close a deal with a client and had a free day and night to sightsee. I browsed the sex shops and ended up buying some white stockings, pink frilly panties, lip gloss, and a white lace bra. I went back to the hotel room and tried on my new sissy uniform and masturbated until my hot sissy cum filled my new frilly panties. Then I put on my swimsuit and headed out to the courtyard pool where I ordered a drink.

There was a woman about 15 years older than me with very large breasts at the bar and I stuck up a conversation with her. We talked about her ex husband and how after 5 years of marriage he left her for another man. She said that although he was gay, they still had the best relationship she had known. And then she abruptly asked me if I was gay too.

“No, I’m not gay. I am very attracted to women. But I enjoy getting in touch with my feminine side from time to time.” I said.

“Well you are a very good listener for a straight man. What do you mean about your feminine side?” She asked.

Usually when I tell a woman I enjoy cross dressing, they run away or assume I am gay, which is why I keep it to myself. But older women seem to accept this better and since I was on a trip, I figured why not.

“I am rather embarrassed to admit this, but sometimes I enjoy dressing up as a sissy. I find it relaxes me and I can have multiple orgasms.” I said shyly.

The older woman then looked deeply into my eyes and took my hand in hers and said, “I find that wonderful that you can share that with me. You know, my ex husband enjoyed that as well and it was one of the things I loved most about our marriage. I miss not being able to do that. I used to love to dress him up in my wedding gown, and I would dress in a man’s suit. And we would pretend to walk down the isle together and then have a honey moon where I was the man, and he was the women. I always thought this strengthened our marriage and bonded us even closer.”

“Wow, that is wonderful. I think very few women are that open minded.” I added.

“Listen”, she said, “I know we just met, but would you like to come upstairs to my room for awhile?”

“Umm, I think I would really enjoy that” I said and the older woman took me by the hand and led me through the hotel and up to her room. I was hard the entire time. I knew that I could really let myself go with this woman and was excited to do so.

“I am going to run you a nice hot bath and then I am going to cover your body with soaps and oils, and pamper you.” She said and looked down at my erection under my swimsuit. “Looks like you are already to go.”

This beautiful mature women slowly removed my swimsuit and my swollen cock popped right out. She eased me into the hot water and began to wash my entire body with soap. She had the caressing fingers of a nurse and I was hers entirely.

“Now stand up sugar and let me dry your bottom off.” She said. “Now stick your butt out a little so I can wash it better. My goodness, your penis just won’t stop looking at me.”

“Now, come into the bedroom here and let’s see what mommy has in her suitcase that might fit her sweetie. Ahh yes. This is very sissy and will look very nice on you.” She said and she took out a pink lace bra and lifted up my arms and slip it down and strapped it on. “Now for panties for my pretty pink sissy. Let’s try on a few of these so I can see which one makes your bottom look the best.” She said as she slipped one pair of panties on me after another. I was completely erect the entire time, just waiting to burst. It was a wonderful torture.

Once she had found a panty that she thought made my ass look good, she began to apply makeup on me.

“There, do you like how pretty mommy has made you?” She asked.

“Yes, very much. You did a wonderful job. Now what can I do to please you?” I asked ready to do anything she wanted.

“Well my pretty pink little sissy. Mommy is very wet in her panties and needs to be serviced. I want you to take those pretty pink sissy lips of yours and go downtown to mommies wet spot and show mommy how much you like being in her sissy things.” She said and she lowered my head to her hot pussy and guided my tongue in circles for her pleasure.

“Now stick you pretty sissy bottom up into the air so mommy can see it while you please me. That’s it, very good, very nice. What a pretty round little sissy bottom you have. All dressed in mommy’s frillies. You love to please mommy don’t you?”

I moaned a yes as I continued to suck on this older woman’s clit. She began to moan too and began to cum all over my face as she held it to her throbbing pussy.

“Oh that’s very good. My new sissy is excellent at pleasing his mommy isn’t he? Now that you have shown you can please me, I think it’s time I get to play with my new sissy toy don’t you? The first thing I need to do is to see how red my sissy’s pink bottom will get when I spank it. Come and lay across mommy’s lap, like you know you have been dying to do.” She said.

I laid my lace stocking thighs across her lace stocking thighs and they glided next to each other in a very sensual and feminine way. I placed my ass up in the air and she began to softly spank me, very gently, and very sweetly.

“You are a very good sissy,” she whispered to me as she spanked me. “You remind me of my ex husband and how much I used to love dressing him up as a sissy. Your pretty pink butt is turning a nice shade of red for me as I spank it. I know how much you like this. I know how much you want to give yourself up to my pleasure and allow me to expose your most secret desire of being feminine. You simply love the feeling of silk and satin and lace as it clings to your muscles. You love being at my mercy and not having to think or make any decisions at all don’t you sweet pink sissy?”

“Oh yes” I cried. “I love it very much.”

“You love being able to be completely submissive to my wise and gentle hands don’t you? You are now my little play toy. My boy toy. My little sexy sissy that I get to do anything I want to don’t you?” She said.

“Oh yes, yes, very much. You know everything. You are wonderful” I said in complete submission.

“And I bet you know what I want to do most to my new sissy toy don’t you?” She asked.

“No, what?” I said.

“Oh now stop lying to me sissy girly boy. We both know what sissy’s like most. You want to have your little sissy butt all full with mommies large strap on. Come on now, tell me what we both already know or else you won’t get it.” She said.

“Yes” I said submissively. “You are exactly right. I want to feel your large strap on buried deep in my sissy ass.”

“Now that’s a good sissy.” She said and stopped spanking me. She lifted me up and told me to go into her suitcase and find her strap on dildo and bring it back. Then she instructed me to assume the position on my hands and knees. She began putting lube on the strap on and then in my ass as she worked it in with a finger.

“I’m just going to move your pink panties to the side because they look so good on you.” She said. Then she began slowly inching her cock into my ass and I began to moan. Then she began to slowly work the large dildo back and forth as my butt muscles stretched for her more and more.

“Now don’t cum just yet sissy. I want to fuck you in many positions first. I want to see you ride my cock like a good sissy every way you can before having an orgasm.” She said.

It was very difficult not to cum as I lay bent on my hands and knees taking her strap on deep into my ass. I heard her moan and cum and then she turned me on my back.

“Now I want to see your face while I fill your sissy hole with my big man cock.” She said. And she bent down and kissed me deeply as she thrust her dildo in and out. Her tongue gouged by entire mouth. “Tell me who owns you now sissy? Tell me who you will always belong to.” She said.

“I’m all yours, now and forever,” I cried out. “I’m your little sissy slut”.

“What a lucky little sissy you are. Now I am going to lie down and I want you to climb on my strap on and show me how well you can fuck it by yourself.” She said.

As I mounted her large strap on, I began to bounce up and down on the cock while she looked deep into my eyes. Her hands rested on my shoulders and guided me up and down to a rhythm she enjoyed. I couldn’t take it anymore and told her I was going to cum.

She pressed her lips to mine and I came all over my panties. I felt incredible and totally relaxed.

“Now hold me and lay with me for awhile.” She said. “Mommy is not quite done with you.”

She stroked my hair and whispered nice and soft things into my ear as we held each other for awhile. Soon she led my mouth to her nipple and to suck on it slowly. And then she began to finger my asshole and in seconds I was hard as a rock again and ready to go.

“Now little sissy, you have earned the right to fuck me. I want you to fuck me just like I just fucked you.” She said and she rolled me on top of her and took my cock out of my panties and slipped it into her wet pussy. I kissed her deeply as I slowly began to fuck this older woman to several orgasms. She reached around and put several of her fingers in my ass and I came instantly.

“Well, it looks like I can fuck you better than you can fuck me sissy. But that’s ok, I am older than you and can teach you many things. Now go and run me a bath and then bath me as I bathed you. And then dress me as I dressed you, and then, if you are good, we can go shopping together and mommy will buy you some wonderful sissy clothes for this evening.” She said.

Sissy Fetish Sex Story Written by Ian for Kinkysexstories.org