Sarah Gets to Write Her Own Story

If you are an adult, looking for some kinky fun, live in the San Francisco peninsula and would like to star in a re-enactment of one of my experiences, contact me. My experiences here show what I like to do. We can write our own scenario and then act it out. I'd love to help you make your fantasy a reality.

Now for my latest adventure, I found a Classified Ad' online that sounded interesting. It was from a girl and she said that she was looking for some kinky fun. It sounded genuine and so I thought that I'd give her a try. I replied saying that I was a crossdresser and loved to role-play in sissy naughty games. I was open to anything safe and legal. She answered me and said that she was interested too and asked me to tell her more about what I would like us to do together. She asked if I liked being 'pegged'. I had to Google it to find out what it meant and decided that it sounded like fun. Also, would I accept dominance, I replied that it all sounded wonderful.

After exchanging a few emails, we agreed on a naughty scenario, as you will cum to find out. It was wonderful planning my own sexual adventure with her and believing that it would really come true.

The day before our first meeting, I went shopping and bought a few props to help with our game. That evening, I packed a bag with my clothes and some other things we might find useful. That night I was so excited I could hardly sleep. I resisted the temptation to masturbate since I wanted to save my cum for the next day. Feeling horny added to the anticipation but it didn't help with getting to sleep.

We had agreed to meet at a local Starbucks and take it from there. I went there dressed as a guy, well, at least as best as I could. I don't own any men's jeans or underwear but I did what I could to look like a guy. I had told her that she would recognize me since I would be wearing a white padded jacket with fur around the hood.

I recognize her immediately; she was gorgeous, late twenties, with long black hair and a cute face. She had told me that she was very feminine except when she was being a Dom.

Our game involved me applying for a job as her house servant. We had a few sips of coffee and then went back to her place. We definitely didn't want anyone overhearing my interview.

Back at her place, she got us drinks and then we sat on the couch for the interview. The scenario said that she could ask me very inappropriate questions, questions easily naughty enough for a lawsuit in real life.

She had put some money on the coffee table and told me that it would be mine if she liked me and decided to give me the job. I told her that I was broke and would do anything she asked of me. That made her smile and say, "We'll have to see just how good you really can be."

First, she asked if I preferred sex with men or women. I said that I went both ways. I liked sex with men for afternoon delight; quick fun with no complications just sex. Most of the time I didn't even know their names and certainly not their real names. When it came to real relationships, I preferred women.

Then she told me to describe the first time I had sucked a cock. I replied that the very first time was at a sex club, ('Sarah Dressed and Visits a Sex Club'). I sucked a guy off while twenty or so other naked guys stood around masturbating and watching us. I only half count this as a first time since he was wearing a condom. The first time I got to taste cum was at a nudist beach, ('Sarah has sex at a Nudist Beach'). Only a couple of other guys watched us but I did end up with cum in my mouth. My first but definitely not my last taste of that wonderful stuff. The taste is always different and stays in my mouth for hours.

Then she asked if I liked having a cock in my butt. I replied that I was new to it but had loved the few times I'd had it done to me. It made me feel so submissive, lying on my back, my legs spread wide, with his erection deep in my arse and completely under his control. She just laughed and said, "I'd love to watch my sissy servant get screwed." This made my heart race. Was she serious?

She told me to stand up and turn around slowly. I did as I was told. Then she told me to strip, I started to argue but she just looked at the money and raised an eyebrow, well I needed the money and so I would take off my shirt.

I actually took off my shirt, shoes and socks and then stood there already very embarrassed. She just smiled and said, 'Keep going'. I said that I only had underwear on under my jeans but she said, "That's what I want to see. I suspect that they are naughty from the way you don't want me to see them."

With trembling fingers, I undid my belt and lowered my zipper. As my jeans fell to the floor, she could see my pink lacy girl's panties. I went red and tried to explain but she just waved me silent. My cock was already excited and added to my embarrassment by making a tent in the front of my panties.

She said I can see that you are wearing girls jeans too, you sissy. She asked me, "You like dressing as a girl don't you?" When I just stammered, she added, "Answer me!!"

I just looked down and said, "Yes".

She ordered me to call her Mistress from then on.

"Say it again; say how much you like wearing sissy girly panties, make me believe you."

I had to say, "Yes mistress, I love wearing sissy girls panties under my girls jeans." since it was true, I guess I convinced her.

She made me turn around so that she could see my butt covered in just wispy lace. I turned back to face her. Next, she told me to take them off too. Well since I was only covered in virtually transparent lace and my cock was clearly pressing forward, I turned my back to her and slipped out of my panties. When I turned back around, I kept my hands covering my now very erect cock but she was nowhere near done with me. She ordered me to put my hands behind my back. I was helpless, I needed the money and so I had to stand in front of her with my cock sticking out.

Smiling with glee, she said that it was time for me to get dressed. I went to pick-up my clothes but she said, "Oh no, I have a uniform for you. You will love it; it will make you into a real sissy."

Well anything would be better than standing there naked with her eyes on my cock. First, I was told to kneel. I was confused but did as she instructed. She got up and went to a bag behind the couch. She pulled out a pair of black ruffled panties; telling me to beg to be allowed to put them on.

I said, "Can I put them on, please" but she made me beg to put them on. I had to say, "Please Mistress, let me put on those sissy panties. I want to feel them against my cock. I want to be a slut."

She handed them to me. I stood up and stepped into them, at least they covered my erection. Well kind of, the net between the ruffles was nearly see through. She laughed at me and called me a sissy. Feel the ruffles and tell me how they feel. I had to say, "Yes Mistress, I love feeling my erection through the sexy material."

Next, she produced a black lace bra. I put it on and then she walked behind me. First, she gave my cock a squeeze and then slipped breast forms into my bra; I had to put a garter belt around my waist. As I pulled on black stockings with white ruffled tops, she could tell that I had put on stockings before. I threaded the garter straps through my panties and fastened the clips. I have to admit that I found it very exciting. My cock was pushing my panties forward but, by now, I was so turned on I didn't care.

I had to walk around while she decided if she liked what she saw. She twanged my garter straps and laughed as they smacked against my thighs. Well I guess she was satisfied because she went back to the bag and pulled out a black satin French Maid dress. It had a white lace petticoat.

I had to step into it and tighten the white drawstring at the front. It came with a black bow to go around my neck. As I stood there, I realized that the dress even including the petticoat was so short I was sure my panties would show if I bent forward at all. I knew that my stocking tops were already clearly visible.

She beckoned me forward and made me kneel, and then she produced a bag of makeup. She applied purple eyeshadow, blue eyeliner and mascara. She used a smudge of lipstick for blush and then red lipstick.

Then came a bag of jewelry. My ears are pierced and so I can wear real girls dangly earrings. She chose a long pink pair with sequins on the studs. A ring, three bracelets and a necklace finished off my accessorizing.

Finally, she produced a shoulder length blonde wig. It was almost the same color blond as my natural hair and really looked good on me. My transformation into a girl was now complete. I had become a slutty French Maid.

To test my domestic skills, I had to go around her place and do some cleaning and tidying. Each time I needed to bend forward, she made me keep my knees straight and bend at the waist. I know she was behind me as she kept putting her hands on my butt to make me bend over even more. All the time I could feel her eyes on my panties.

She even put a hand between my legs to keep my knees apart. When I had to bend to the ground, I know she could see my balls cupped in my parties.

She asked me if I masturbated, how often and what I looked at while doing it. I said, "Yes Mistress, I masturbate every day. I deliberately make myself hard and then stop. Stopping extends the anticipation of when I finally make myself cum. I love putting my hand in my pocket and touching my cock. I love exciting it until I nearly cum, with one pair of jeans, I had cut a hole in the pocket so I could touch myself skin to skin."

She said, "I WILL enjoy watching you cum."

I noticed the very clear 'will'. She would make me do it while she watched me.

I told her that while masturbating, I found it very erotic to watch Crossdressing videos showing girls giving blowjobs and being fucked. I especially like the forced feminization videos with guys pretending to resist while loving every moment of it. This made her smile in a knowing way that thrilled me. What else had she in mind for me?

By now, I was blushing like mad and still trying to protest but she would just smile, knowing that I was really loving it.

Then she commented that I was also an exhibitionist slut, she asked if I like it when people watched me having sex. I had to admit that I loved being watched while I suck a cock or got my arse fucked.

I had to tell her about other times I had a cock in my mouth. I said I used to advertise on Craigslist personals and offer to give blowjobs. As soon as I let a customer in and closed the front door, I would drop to my knees and stroked his crutch. I outline his cock with my fingers. It was wonderful wondering what it would look like and how his cum would taste. Every time it was different.

I'd look up into his eyes and lick my lips. We both knew exactly where we were going. I'd undo his belt and slowly lower his zipper making sure my fingers ran over his cock as I did it. With another lick to wet my lips I'd take his cock out and slip my lips around the head. To start, I would just lick around the helmet. Slowly, I'd go lower until I took all I could into my mouth. I would run my tongue up-and-down his shaft and tweak his pubic hair.

I wouldn't spend too long at it since I didn't want him to cum just yet. This was to get him excited and expectant of more to come.

She asked me where I got my clothes. I explained that the special stuff usually came from Amazon, for daywear I got many things at Goodwill. I did love Fredericks of Hollywood but they closed. When I shopped there for panties, I always accepted the sales assistant's offer to help me. I made it clear that the panties were for me. I said things like, 'I love pink with bows' and 'No I didn't need a gift receipt. I like what I've chosen'.

I loved to watch her fold them and wrap them in tissue paper. I thought about how they would soon have my cock in them. Sometimes, I even asked to use the changing room so I could wear a pair to go. Walking out I loved nodding at her knowing that she knew what I was wearing.

She ordered me to go and get us another drink. After the coffee and a couple of beers, I needed to pee. She insisted that she would come with me to help. She stood behind me, took out my cock and held it while I peed. It was hard to let it come with her hand wrapped around my cock, I found it incredibly erotic, and not in my script. As she shook me dry, she pressed against my butt.

She said that I was doing well but I still had a couple more tests to pass. First, I had to please her. She stood up and slipped off her jeans. I was not surprised to see that she wasn't wearing any panties. She sat back down, skootched forward and spread her legs. I had to kneel in front of her and lick her pussy. I did it the same way I give head.

I started by stroking her inner thighs. Slowly, my fingers crept up to her mound. I ran my fingers through her pubic hair. Leaning toward I gently sucked on her hairs. I let my tongue just touch her pussy lips. At first, I just barely made contact as I ran it around her lips.

Very slowly, I pushed my tongue into her. I finally found her clit. It was already very excited. She grabbed my head and pushed her pussy hard against my mouth. Our lips were pressed together. I moved my lips to massage her pussy. My nose was buried in her hair and I tried to move it to stimulate her even more. I could feel her climax building. As she came, she squeezed her thighs around my head. With her feet on my back, it felt just like when I give head. She finally fell back exhausted for a few minutes. I licked my lips and enjoyed the taste of her juices.

When she had recovered, she made me kneel with my face buried in the cushions. I had to lift up my skirt and stay there with my panties and stockings on show. She got up and I heard her doing something behind me. Then she told me to turn around and open my mouth. She had put on a black strap on dildo. She pushed it towards my mouth and told me to give it a blowjob.

I stammered that it looked like a man's cock. She just laughed and said, "That's why I want you to suck it you slut. I know you love having a cock in your mouth. For today, this is the best I can do but next time we'll have to see what I can find for you to suck. You'd love to have a real cock in your mouth wouldn't you?"

I had to say, "Yes Mistress, I would love to have you watch me suck a real man's cock, right in front of you and show you his cum in my mouth at the end."

I closed my eyes and imagined that the dildo was the real thing. That way I was able to demonstrate how well I suck cock. I was excited thinking what she meant by 'next time'.

Then she had me turn back to the couch. I felt her applying something cold to my arsehole. Then I felt the dildo pushing into me. I loved it. As she fucked me, it felt just like a real cock pushing into me. I felt her pubic hair press against my butt. She reached around me and played with my balls. I was groaning by now. My cock felt like it would explode. When she gripped it and started to masturbate me in time with her fucking me, I came; I collapsed forward to get my breath back.

After a few moments, I sat up and smoothed down my dress. She had taken the chance to finish stripping. She was smiling and said, 'Congratulations you have the job. Now your first task is to help me shower. Strip and come with me.'

I took off my uniform and went with her into the bathroom. The shower stall was a normal home shower and so we were pushed together. It was wonderful, slippery soapy wet skin to skin. With the space available, we had to wash each other.

She took the soap and started washing my cock and balls. I took some shampoo and washed her pussy. Working my fingers through her pubic hair.

Then she pushed her finger into my butt and so I did the same to her. My now erect cock was squeezed between her legs. She produced another dildo from somewhere and pushed it into me. With all the lube still in me and the soap, it went in quite easily. We fucked each other's butts and started kissing. I think we both came again. It was hard to tell since we were so closely pressed together and passionate.

We dried off and she went and got a pair of powder blue panties for me to wear.

Before I left, she gave me some homework.

Next time we met at Starbucks I must arrive dressed as a girl and wearing her panties. While sitting there, I must slip them off and slide them across the table to her. I could be as discreet as I wanted to be, saying this with a wink. I knew she would love to see me embarrassed in public. I was sure I'd get an erection and without panties on it was bound to show. Her ideas excited me; I could hardly wait for next time.

Second, I must think up some more scenarios for us to play out. I started thinking about a scenario where we would go shopping together for lingerie and she would tell the shop assistant that I needed a matching bra and panties, pink would be nice. I would blush and stammer but she would just say, "Be quiet you sissy girl. You always look so cute in pink."

Third, I must assemble a school-girl outfit. We would play French Maid again but we also needed other ideas. Amazon here I come. Short red pleated skirt to start with.

Before I left, she came up to me, felt my crutch, and said, 'You were a really good girl. I WILL have lots of fun with you in the future.'

I left with my cock spent, my butt sore and my mind working on new ideas. All I had to do was think up a fantasy and it might come true. I realized that I wasn't going to be the only one thinking up ideas, she had already added a couple of things to my scenario.

I wonder what she will think of this our first experience together. I was careful not to give away any identifying details.