Mr. Simms Has Pics of Me in a Dress



“Hello Jaime.” said my neighbor, Mr. Simms, smiling, when he opened the door to his house. It was very nice two-story brick home in suburbs, probably around 3,800 square feet.

“Hello sir”, I replied. I looked up at him, he was at least a foot taller than me, and he shook my hand, then, waived me to come inside.

Mr. Simms lived right next to us with his son, Charlie, who was about my age, 18. Charlie and I were seniors at the same high school, but, we hardly knew each other. He hung out with the athletic and popular kids, but, I was much lower on the totem pole and something of a loner.

Charlie had gone to spend the summer with his mother. Mr. Simms was divorced. His wife had left hims several years ago and she lived in Florida now with her new husband.

I had ran into Mr. Simms earlier in the week when I was walking my dog and he was picking up his mail. He smiled at me and asked me started to talk to me.

He asked me what I planned to do over the summer.

I told him I was taking some classes to get a head start on my first year of college, and, I would also be looking for a summer job.

Mr. Simms was an accountant who had his office in his home. He asked me if I would be interested in working for him over the summer as a clerk. He said he would pay me $15 an hour.

That was a lot better than what other places would offer, so, I told him I would like to do that, but, I knew nothing about accounting. He said, as his clerk, I would mostly just set up files and keep them organized, track information requested from clients and schedule his appointments.

We walked into his office, which was large and looked very professional. He had a big mahogany desk, with a big leather executive chair and two arm chairs on the other side of the desk. He also had two long wooden filing cabinets.

He sat at his big leather chair and I sat awkwardly in one of the two chairs facing him.

Mr. Simms stared at me for a while with a smile, but then, his smile seemed to shift into something more serious.

“I have to tell you something, Jaime.” He said. “If I am going to trust you with my files, I have to be sure you are 100% honest with me. These files have extremely sensitive financial and confidential information.” He said.

“I understand Mr. Simms.”

He took a breath and then, went straight to the point.

“Well then, Jaime. Tell me honestly, are you gay?”

I was stunned by this question. I couldn’t believe he had asked me that. How is that relevant to anything?

But, I did not protest. I answered, “No sir, of course not.”

“Ah, okay.” He answered.

“Are you a transvestite?” He asked.

This question was even more shocking than the first, and, I felt the wind knocked out of me as if someone had just punched me in the stomach.

“No sir, of course not!” I said. I hoped he could not detect the nervousness in my voice.

There is no way he could know anything, I told myself.

“Um, okay.” said Mr. Simms nonchalantly.

Then, he opened up the top drawer on his desk and pulled out six pictures and laid them on the desk in front of me.

My jaw dropped and I gasped! Oh my God!

“No!” was all that could come out of my mouth.

“That’s not me!” I said, even though the denial was ridiculous.

How? When? – I asked myself. My face must have been as pale and white as a ghost.

I had different outfits on in the pictures. He must have taken these pictures on different days. How long had he been spying on me?

I did not have a lot of girly clothes. I had one black dress that I had stolen from my aunt a weekend that she stayed with us. She was petite and thin, just like me, and she wore the dress to go dancing in the city with her old friends. It was a sexy mini dress that hugged all her curves with velvety and stretchy fabric. It was so small, that she could not bend over to pick anything up. I got rock hard when I saw her in that dress and I was very confused. My aunt was younger than my mom and not bad looking, but, am I getting a boner for my aunt? I had never thought about her like that before. I realized later that it was the dress that had gotten me so turned on. – A dress? – Yes, I had the urge to take it and use it to masturbate, though how I would use was not apparent to me right away.

I borrowed it the next day, because, I wanted to touch it and hold it so bad. Then, when I was alone in my room with the dress, I felt a strange and powerful urge to put Pendik Anal Escort it on. I resisted the urge a little, because it seemed like a very weird and gay thing, but, the urge just got stronger and stronger. Finally, I could resist it no longer.

I got naked and put the black dress on. It felt wonderful on my skin. Then, I looked in the mirror and I could not believe it! I did not see a short scrawny unattractive teenage guy, Instead, I saw a hot little chick in a hot mini dress! The dress even made my face look cute and girly and I got so turned on just looking at myself!

I got on my tippy toes, as if I was wearing high heels, and I bend down to see the dress lift to show my ass. I tried many different poses, some just innocent girly poses, and some, more risque.

I became more and more aroused by this, until I started masturbating, and when I came, I discovered that playing with girly outfits gave me orgasms that were many times stronger than normal jacking off. Looking like a teenage hussy was so much more sexually thrilling than fantasies of banging them!

I played with girly clothes again, and again, and many more times after that. I managed to steal a few other things: two short skirts from my sister, a sheer pantyhose and opaque thigh high stockings from my mother, a blouse and fishnet stockings from my sister’s Halloween costume, and two panties and one bra from my mother. I did not steal more than one item at once, so as not to make anyone suspicious.

Although playing with girly clothes became a very exciting thing for me, I felt very ashamed of myself afterwards. I knew it was not what normal boys did.

I thought I could hide this queer thing forever, but, my day of reckoning had arrived! Life as I know it is over for me.

I was terrified of what Mr. Simms would say next. I put my head down and covered my face with my palms, I cried and I felt nauseated.

Mr. Simms said, “No, don’t cry. I did not mean to upset you. Please stop crying.” He got up and brought me a pitcher of water and a glass. I drank some water.

After giving me a few minutes to compose myself, Mr. Simms, finally said, “I am not trying to embarrass you. You look great in those pictures, don’t feel ashamed.”

“I thought I might be able to help you.” He said.

I stopped crying and looked up at him. What did he just say? How could he help me? Does he know a way to make these perverse urges stop?

“First of all, we need to be honest with each other, okay?” He said.

He looked straight into my eyes, then, glanced away and said, “I know what it is like to be wired a little different from other men.”

Wired differently? This odd comment made me curious and I asked him, “What do you mean?”

He hesitated for a minute, and then he finally said, “My wife left me because she found out about my porn addiction.”

He paused, then said, “I’m not talking about normal porn that men watch. I am not gay, but, I got hooked on porn that involved middle-aged men with submissive feminine young men.”

He paused, again, then said, “I am not gay. I love women. But, there is some weird wiring in my brain that makes this kind of thing sexually arousing to me.” He said pointing at his head.

My mind was trying to process all this. What was going on here? Mr. Simms’ revelation of his sexual attraction for young men was making alarms go off blaring in my head! Did he want to use me for sex? Is that what this was all about?

I felt very scared and nauseous.

Mr. Simms explained, “My cat had gone missing for two days. It likes to perch itself up on roofs. I walked around the neighborhood with my binoculars looking all over for it.”

He continued, “Imagine my surprise when I was looking around your window and spotted a gorgeous young woman in fishnet stockings trying on a sexy black cocktail dress. I knew it was rude to watch and I wanted to look away, honestly, but, I couldn’t. I was really getting turned on. But, then, when you pulled out your dick and started to masturbate, I was shocked! What the fuck! The beautiful young girl I had been admiring has a dick! Then, I realized it was you. Strangely, I got even more turned on after realizing it was you.

I blushed beat red and covered my face with my palms.

“That was the night I took this picture. I ran back home to grab my camera. I wanted to capture that image of you. It was very sexy!”

He took a breath and said, “You are lucky no one else has seen what I Pendik Yaşlı Escort have seen. You close your curtains most of the times, but, not always. It seems that when you are the most excited and anxious, you get careless and completely forget about the curtains!”

I felt so ashamed and so stupid.

Yuck! I can’t believe Mr. Simms has been watching me. Had he masturbated while watching me? I felt used and dirty! This was just too gross! I wanted to vomit.

So, why had Mr. Simms brought me to his house? Is he planning to blackmail me into having sex with him? I was beginning to hyperventilate and panic! Oh God! I cannot become a middle-aged man’s bitch!

I finally blurted out, “Mr. Simms!” I tried to sound manly and tough, but, my voice was weak and cracking.

“Please, sir!” I paused to breath, “Please do not force me to have sex with you! Please don’t make me!” My voice broke and I was in tears.

He looked straight at me and his face turned into the expression of anger.

“Did I say anything about us having sex?” He asked angrily.

“What kind of monster do you take me for? You are way off base making that accusation and I should ask you to leave right now.” He said, sounding very upset.

“I’m sorry, Mr. Simms.” I said softly and he seemed to soften up.

He finally said, “Jaime, I am not going to force you to do anything, so don’t worry about that.”

Then, he said, “I bet you would love to have a safe place to play dress up. And, I bet you would love to have lots of new clothes, anything at all that you desire. I bet you would love some high heels, make-up and a wigs.”

He added, “Come to work for me and you can dress as a girl for hours while you are here. My client appointments are usually out of the office, so, we will be alone here.”

He quickly added, “And you have my word, I will not make any unwanted physical advances. I am happy just to look at you. I think you are very attractive, but, I have plenty of self-control.”

My body froze as my mind raced. A place to dress-up without fear of being caught, I could stay dress-up for hours, I could have all outfits I wanted, and I could finally add make-up and wigs to my dress-up play!!!

“I have a very simple proposition to you. Come work for me this summer as my clerk; no better as my sexy secretary. I’ll buy you any things you’ll love to wear – dresses, skirts, shoes, make-up, wigs, breast forms, whatever!” He promised.

I was stunned by the offer. I knew that, even if he did not touch me physically, he would be using me as masturbation material in his mind. I knew I should reject the offer.

But, fuck! I CAN’T!!! As long as I did not see him jerk-off, what difference is it to me. Everyone jacks off, right?

I just want to get dolled up! I get an incredible rush and incredibly excited when I dress up! My heart was beating fast from just thinking about it! No more rushing through my dressing up and feeling terrified of getting caught by my parents! I could really reach my full potential of looking hot!!!

I wanted to act nonchalantly, like this proposal was not a big deal to me, but, I was already wetting my briefs with all my excitement! Right now, it was lucky for me that my dick was very small and that I could hide my erection.

I kept quiet for a minute trying to calm my excitement before replying to the proposal.

“I swear to you that I will be a perfect gentleman.” I promised.

“Yes!” I finally blurted out. It came out as an excited utterance, even though I had tried to cool off!

I was really tired of wearing the same outfits every time and I would kill for new outfits! And, make-up. Oh, I’ve wanted to try on make-up so badly! I have watched youtube videos on make-up, but, I would never take such a big risk in my parent’s house.

So many ideas raced through my mind of what I could do with this opportunity! My imagination ran wild! I saw myself dolled up and looking stunning. I even saw a tall guy standing next to me. What? Why is there a guy in my daydreams? I am not gay!

But, my imagination kept running. It was not about to stop to answer my question. The mystery guy held me firmly from behind by my waist, as if asserting his possession of me. Then, in this daydream, I turned to see his face, and, it was the face of Mr. Simms!

Shocked, I finally awoke up from my daydreaming. Mr. Simms was standing right in front of me!

“Are you okay?” He said.

“Yes, I’m fine. Thank you.” Pendik Zenci Escort I answered. Oh my God, my voice came out like a girl’s voice!

Mr. Simms smiled and said, “Well then, it’s all settled. You can start on Monday. I need plenty of help organizing new files. You can bring, you know, anything you want to wear, and, I may pick up a few gifts for you. You can give me a list on Monday of anything else you would like to have. I’ll give you a clothes allowance of $500.00 per month, and, if you need more than that, I can give you an advance on your paycheck.”

“We need a secretary name for you.” He said.

I had not thought about that, but, it made sense to have a girl’s name when I dressed like a girl.

“I don’t know. I’ve never thought of one. Can you pick one out for me?” I asked him.

“How about Carmen? I used to know a really hot little Latin beauty with that name.” He said.

In my mind I said in a soft and sensual imaginary voice – My name is Carmen. I love it!

I got up from my chair, feeling light-headed from the unusual and surreal events that had unfolded.

I looked up at Mr. Simms, and made eye contact with him. Then, I felt embarassed and glanced down.

Mr. Simms and I stood awkwardly smiling at each other for a minute, and then, we walked to the door.

We shook hands very awkwardly. I noticed for the first time that he had very big and strong hands, and, something about this made my body tingle.

When I got back to my house, I was so damn horny that I ran to my room to masturbate. I did not even wait to take all my clothes off. I did not even put any girly clothes on, because, I had already been doing that in my head!

I had not realized that I had been building up an arousal and that I was extremely horny!

I writhed in bed like a bitch in heat stroking myself and squeezing my nipples and my ass. I had to bite hard on my teeth to stop myself from moaning and grunting.

I thought about wearing new dresses, skirts and stilettos, and make-up. Then, without meaning to, my mind started to think about Mr. Simms. I wondered if he was also masturbating right now. I thought about him stroking his cock.

I wondered what his cock looked like; how thick and how long it was. I wondered what his pre-cum looks like. Why was I thinking about this right now? Gross!

The images just came to me. Mr. Simms standing tall, naked, muscular, holding his big thick and long cock in his big right hand with cum oozing and dripping.

No! I don’t want to think about Mr. Simms right now!

But, my mind would not let go of Mr. Simms. I kept seeing Mr. Simms’ cock. It was at my eye level only a few inches from my face. It was large and firm and it was throbbing and dripping with pre-cum and begging for me to touch it.

There was no use fighting these images in my mind, so, I actually stretched out my free hand as if to grab his cock.

I suddenly felt an electric shock and my back arched and I bit my lip, as I started to experience the first wave of most intense orgasm of my life!

My dick exploded like never before and my orgasm lasted longer than ever before. I made a terrible big mess on my clothes and my bed, and, I was dizzy from the intensity of this experience.

When I could finally think again, I cleaned myself. I cleaned my clothes and the bed as best as I could.

What the hell was that? – I wondered.

Okay, it was normal for me to think about girly clothes while I masturbate – the soft and sensual feeling on my skin – and how feminine and sensual and beautiful they make me look.

But, why did I have images of Mr. Simms swimming in my mind? I was disturbed by this, so, I tried to be analytical about it.

Mr. Simms was giving me an opportunity to dress up and he was going to buy me all the clothes I wanted. Also, he had confessed that he was attracted to me. So, maybe I was thankful to him. Maybe I just appreciated him.

I thought about it and I realized it was actually very flattering that he said such nice things about how I look as a girl. It was the first time in my life that anyone has said anything nice about my looks.

So, that was it. I guess I just appreciate his kindness and validation. That’s all it means. I convinced myself it was not a big deal.

Oh shit! I suddenly realized that my curtains had been open the whole time! I ran to the curtains and closed them.

Damn it! What if he had been looking at me this whole time?

I tried to calm myself down. I did not want to worry about anything right now. I had just experienced a pretty damn awesome orgasm and my body was still tingling.

I just wanted to relax and fall into my post-orgasm bliss. I smiled and curled up in bed and fell into a profound sleep.