The Yellow Dress
After my mom and dad divorced, a couple of years later my mom married a pretty nice guy named Phil who has a son, Ted, and a daughter, Kate, from his previous marriage. Phil has custody of his kids only during the summer so as soon as school let out in early June, Ted and Kate flew to our town and moved into our house. I had only met Ted and Kate once before which was six months earlier at my mom's wedding and I thought they were pretty cool kids. Ted is two year older than I am and Kate is a year older and I have to admit that Kate is very pretty and I was and am somewhat smitten by her. I particularly love the way that she looked in her pretty flower girl dress at the wedding.
After Ted and Kate arrived at our house, at the first available opportunity I scouted out Kate's closet and dresser to see what clothes she had brought with her for the summer. She had a pretty nice assortment of panties and bras and an especially nice pink bra and panty girdle set that attracted me. The highlight, however, was a gorgeous, pale yellow sun dress hanging in her closet. It was of a soft cotton, with a gathered shirring at the bust and a marvelous billowing skirt that I fell immediately in love with.
I had to wait almost a week, on a Tuesday morning, until my mom and Phil were both at work, Ted was away with a new friend he had made playing baseball at a nearby park and Kate had biked to a summer ballet class that she had enrolled in. Finally, alone in the house, I had the opportunity to wear the yellow dress.
I first put on one of Kate's panties and a bra, taken from her laundry basket since I didn't want to arouse suspicion. I also stuffed a panty into each bra cup and then put on her yellow dress. I'm pretty sure I had never felt so happy in my life as when I looked in the full length mirror in my mom's bedroom to see my image. The dress was every bit as pretty on me as I imagined it would be and I felt like I was a girl gazing at her pretty figure in the mirror.
I went and sat down in the living room carefully spreading the skirts of the dress around me. I felt demure and pretty and I closed my eyes and allowed myself the wonderful pleasure of basking in my femininity. How nice it would be if I were a girl and then I wouldn't have to depend on only grabbing moments of peace and joy like this one.
Keeping my eye on the clock, I went back up to my mom's room and gazed at myself in the mirror. I must have been there about 5 minutes or so trying out different girlish poses in the mirror when I was shocked to see Ted's face in the mirror behind me. I shrieked and swiveled around violently and attempted to run around him to my bedroom but he caught my arm and said, "stay right here!"
I froze in place, looking down at the ground with my mind racing through all the horrible, embarrassing scenarios that I now would have to face from my mom and Phil and Kate and God knows who else. "I'm sorry Ted, I don't know what to say. Are you going to tell your dad?"
Ted looked at me and said, "what the fuck is this Greg?"
"I'm sorry. I was just curious."
"This is more than curiosity Greg. Wearing my sister's dress. Are you gay?"
"No, Ted. I just like pretending I'm a girl."
I nodded my head vigorously.
"How long have you been doing this?" he asked.
"A few years Ted. I've worn some of my mom's clothes." I was not lying. I had often worn my mom's bra and girdles, always taken from the laundry. Her dresses were too big for me and I never wore them. "Are you going to tell? I promise you I'll never do this again."
Ted looked me over and said, "Kate won't be back for an hour. Come with me."
I followed Ted to his bedroom where he had me sit next to him on a small sofa that faced his television set. Ted said, "I'm not going to say anything to anyone about this on one condition."
"What's that?" I asked plaintively.
"That you do everything I say for you to do without any complaints," Ted said. "If you complain I'll just go ahead and tell my dad."
"What sort of things?" I said.
"Yes or no?" Ted said.
It was not a hard choice to make so I said, "sure, I'll do whatever you say." I was resigned to my fate.
"Smart move Greg," Ted said. "Now sit back and relax. I'll turn on a show to watch."
Ted turned the TV on and we began watching an episode of Bonanza. "I love Bonanza," Ted said, "but I can never figure out why four eligible guys are happy to live on a ranch without any girl friends."
While Ted said this I watched as he undid the button to his shorts and then unzipped his zipper. To my surprise he reached in his underwear and after sightly sitting up so as to pull his shorts down a little, took out his penis.
"Ted?" I said, "why...?"
Before I could ask him why he had done what he had done Ted said, "I have to admit that you look like a pretty girl in that dress Greg and you've already told me that you want to pretend to be a girl, so here's your chance. I want you to give me a hand job."
"A hand job?" I repeated. I was about to ask him if he was serious, until the look on his face made me realize that this was no game. The intensity of his gaze communicated everything. Either give him a hand job, or he would spill the beans.
"Sure Ted," I said. Ted turned away from me to watch the show and I gingerly reached across his lap to touch his penis with my hand. I had never touched a penis other than my own before and it took great effort to force myself to touch his cock. It was warm and kind of very soft. I looked up at Ted who was watching Bonanza and he said without looking at me, "let's get on with it Greg."
At that moment I realized that as long as I allowed myself to pretend to be a girl in the yellow dress then it wouldn't be so hard to touch Ted. That was exactly it. I would be a pretty girl and I would touch Ted's penis like any girl would and I would get him to cum. That was precisely what I had to do. Shut out everything else and be the girl I wanted to be.
I gently encircled Ted's penis in my hand and moved it slightly. Almost instantly his penis hardened a little and I felt surprised at the power I had acquired in my hand to give pleasure. I moved my hand now up and down very slowly and slided it around the cock using my finger tips to touch various spots underneath the sensitive tip. Suddenly Ted's penis shot up into a boner and stood up all by itself. I now had more room to slide my hand up and down the shaft. I used my palm to touch the underside and applied slight pressure with fingers along the side.
I glanced at the erect penis and watched the movement of my hand. It was an interesting sight to watch another boys' penis juxtaposed on my hand. His penis was much longer than mine, and there was some pubic hair surrounding its base and what appeared to be firm balls. I wondered what it felt like to touch the balls and I let my hand surround them gently. Ted moaned loudly. I looked up at his face and I was pretty sure that he was no longer looking at Bonanza.
"Use some spittle," Ted said, "so you can slide easily."
Ted was right. As long as his penis was dry to the touch it was hard to get the kind of rhythmic motion going that I would need to get him to cum. I noticed a drop of precum at the top of his penis and I used my finger to spread it around the shaft. Then I licked my hand and added more saliva to it and placed it on his penis. I repeated this a couple more times until his penis was slippery to the touch. I now was able to easily slide my hand up and down his cock. I felt the increasing tightness and solidity of his member at it inched closer and closer to a point where Ted would orgasm.
I looked down at my pretty yellow dress as I stroked Ted's penis. I could see the small outlines of my bust created by the panties in my bra and I told myself that I probably ought to use two panties in each cup so I could be even more shapely. That would be nice. And I wondered what other bras and panties of Kate's that I might one day get to wear. The bra and panty I was wearing were white and had little bows in the front. It would be so much fun to wear the pink panty girdle I had seen. Unfortunately it hadn't been in the laundry.
I could sense that Ted was close to cuming now. Every pass up toward the tip caused his penis to get rock hard and he was making a steady stream of moaning sounds. Then I slowly increased the pace of my stroking and he said, "get a tissue and catch it!"
I looked around and saw a nearby tissue box and took a couple of tissues. In the next instant Ted let out a yelp and as his penis began spasming I quickly used the Kleenex in my free hand to catch his cum as it came flying out, and then mopped it up as it dribbled down the side of his penis to his pubic hair.
Ted took a few moments to calm down and relax and then opened his eyes and looked at me. "I wish you were a girl Greg. You're a natural."
I didn't know if I was supposed to thank Ted for the compliment but I said "thank you."
"Actually," Ted said, "I feel pretty badly about forcing you to do this. That's not the type of guy I normally am, but something about the fact that you looked like a real girl and that you were wearing my sister's clothes made me want to even the score."
I looked at Ted and said, "it was wrong of me to wear Kate's clothes. That's something I did that I regret. I don't blame you for wanting to make me pay for that."
"But it means a lot to you to wear her clothes, doesn't it?"
I nodded my head. "Well, how about, every Tuesday I'll have you do this again," Ted said. "You can wear the yellow dress and you can give me a hand job. Just like today. No one will ever be the wiser."
I was overcome with a strange emotion. It was a kind of tenderness for Ted as well as relief that he'd give me the opportunity to be a girl again in the same way. It was something that I could look forward to each week and especially make plans to get better and better at being a girl.
The following Tuesday as soon as Ted and I were alone, he told me to go to his sister's room and get dressed. Once again I found a nice bra and panty in her hamper to wear and then put on her yellow dress. As before Ted had me sit next to him and play with his penis. He insisted I go slowly this time. We were in no rush and so with the TV playing softly I gently moved my hand over his swelled member. I tried touching different parts of it in different ways and made mental notes of which particular movements caused him to stiffen and even to moan in pleasure. Even more so than the first week I relaxed and let myself feel like I was a real girl on a date with her boy friend. This was what girls could do for their boy friends if they wanted to and I felt happy that I could give Ted this attention and make him happy. This time I had put two panties in each bra cup and I loved looking down at my more prominent chest. It helped me feel more girlish. Looking at my bare legs I wondered if perhaps Kate had some pantyhose that I could put on. That would definitely be a fun thing to do in the future.
After what must have been close to an hour, Ted said it was time to finish him off and so I initiated the steady, slowly accelerating stroking that caused him to shoot off. He gave off a scream of ecstasy at the very end and as he lay there recovering I cleaned him up. He said, "that was the best orgasm I ever had in my life."
"Thank you Ted," I said. "It was actually kind of fun to do it and I'm glad your happy."
The next two Tuesdays enfolded very much like the first two Tuesdays. However, on the fifth Tuesday Ted seemed a little distracted like he was planning something different. When we sat down in his bedroom this time, instead of turning on his TV, Ted put on some background music and drew the thick shades so the room was fairly dark. I could barely make out Ted's features in the gloomy room. "What's happening?" I asked Ted with some anxiety. Clearly there was some reason why he wanted the room dark.
"I hope you're not mad at me, but I sort of bragged to my friend Fred that I had a girl friend who jacked me off. So then one thing led to another and I invited him over here. Do you mind doing that to him? I figured its not worse than what you already do and you don't seem to mind doing it at all."
"Well I guess I could do it. Just like I do for you? Just touch his penis and make him cum?"
"That's all, only one other thing is that I told him that your name is Amy. You're a girl I know. Can you do that?"
"Amy? Well sure I guess so."
"You be Amy and I ..."
At that moment the doorbell rang and I jumped up in a panic but Ted said, "don't worry that's Fred. You're Amy remember? Act like Amy and don't talk. You're just a girl I happen to know."
Ted left the room to answer the doorbell. I could hear from his bedroom the sound of foot steps as he and someone else climbed the stairs. A second later Ted entered the dark room with another guy whose features were not clearly visible. Ted said, "here's my girlfriend Amy I was telling you about."
The other guy said, "she's for real! I thought you were bullshitting me."
"She likes doing it. Anyway, she's happy to do it to you the same way she does it for me. Just like I said."
"Amy, this is my buddy Fred. I told him that you didn't mind working on him the same time you work on me? Is it still OK?"
Ted had told me not to speak so I nodded my head.
"Great! You sit down over there Fred," Ted said indicating my right side, while he sat down on my left side.
"Ain't this cozy," Fred said. "She's really going to do it?"
"Just pull down your pants and take it out," Ted said as he unbuckled his belt, unbuttoned his shorts and pulled down his zipper. He then let his pants fall to his ankles and then he pulled down his underpants. Fred stood up and did the same. I was used to Ted's penis and I wondered what I'd find out about Fred's. From what I could make out in the dark his was about the same size as Ted's but maybe a tad bigger. He had more pubic hair than Ted did.
Ted and Fred sat down and I didn't hesitate to reach out to both of their cocks. Fred's with my right hand and Ted's with my left hand. It was an interesting comparison to make as I felt the two penises. Fred's seemed a bit heavier but more responsive than Ted's. Fred had already arrived at a boner and I had barely touched it. I knew that Ted wanted me to play with their penises for about an hour so I touched them gently and continually varied the parts I had contact with. It ended up being easier to put my main focus on one of the cocks, working to get it hard and leaking precum, to then move my concentration to the other cock. While I focused on one cock my hand roamed randomly over the other one, occasionally hitting upon the most sensitive areas. Most of the time I seemed to have a hard cock in one hand and a softer cock in the other. The first time I got Fred up to a full erection I could feel that his cock was perhaps not really longer than Ted's but it certainly was thicker. I had a different kind of feeling in my palm compared to Ted's as I ran my hand up and down along it. Fred's balls were also bigger and firmer than Ted's and somewhat easier to grab a hold of during the occasional moment that I caressed them.
We went on like this for quite some time and then Ted indicated that I needed to finish. I began simultaneously stroking both cocks with my palms running against their soft undersides. I first stroked them simultaneously, but then switched to stroking them back and forth going from one to the other. This allowed me to be somewhat more forceful and the result was an intermingling of little shrieks of pleasure from the two guys. In my mind it became a contest as to who would cum first and to my surprise they both seemed to ejaculate at the same moment letting out loud yells of pleasure. Since I had no way of catching the effluent it just shot all over Ted's rug and sofa as well as onto their pants and underwear lying at their feet. After I released my grip on their penises I grabbed some tissues and cleaned them both up as best I could. Luckily none of their output landed on the skirt of Kate's pretty yellow dress.
For the rest of the summer I mostly had two guys to service on Tuesdays, though some days Fred didn't show up and Ted said that he had to be away with his family on trips to the beach and to his extended family. The freedom to wear the yellow dress and Kate's underwear without worry or concern more than made up for the fact that I had to work on Ted and Fred's cocks at the same time. In any event, I enjoyed the opportunity to be as much of a girl as I could be and certainly giving them hand jobs helped me feel like I was performing a feminine role.
As the days went by and it was getting close to the inevitable day when Ted and Kate packed up their things and headed back to living with their mom, I grew apprehensive about the loss of the yellow dress. I had grown close to it and even felt that it was sort of mine. After all, Kate had not worn it the entire summer. She probably didn't even remember that she had it.
On the last Tuesday that Ted and I would be free to act out our little game he told me that Fred was away and it would be just the two of us. When we were alone I went to Kate's room as was my custom to get dressed. Looking in her hamper I was overjoyed to see that finally her pink panty girdle with matching bra was in the laundry. Ever since I had seen them the first week of the summer I had coveted the opportunity to wear them. I remembered that a couple of days earlier Kate had gone with her ballet class to attend a performance of a visiting dance company and she had gotten specially dressed up. No doubt she had worn her pretty pink bra and panty girdle that night. What a wonderfully perfect, if not bitter sweet, end to my borrowing of her clothes.
The panty girdle was made of a kind of shimmery or sparkly pink material that offered much more support than a panty. Stepping into it and pulling it up my legs I loved the way it hugged my thighs and then slipped around my butt and held me tightly, without being too tight or uncomfortable. Just a nice secure feeling. The bra was equally luxurious with a pretty cotton candy shade of pink and cups with some lace and a bow in the middle. I stuffed three panties into each cup this time and was thrilled at how bosomy I felt. I put on the yellow dress and stood in front of the mirror enjoying the wondrous female image I made.
I went to join Ted and when he saw me I saw him react with some surprise, "wow Greg, you look really sexy today!"
I laughed and said, "I was so happy cause I finally got to wear Kate's pink panty girdle and bra. All summer long she didn't wear them but finally she did. They're so pretty."
"If you say so," Ted said obviously not sharing my excitement.
With a summer's worth of experience in playing with Ted's dick and feeling extra motivation coming from the gentle feminine tug of the panty girdle and bra within the yellow dress, I sent Ted to heights of sexual pleasure that he had never felt before. I had his penis so hard for so long that his legs would not stop shaking and he let out a continual moan only broken by sudden rapid fire panting. Suddenly, Ted put his hand on mine and pulled it away from his cock. He turned to look at me and said, "I can understand if you refuse, and I won't hold it against you or even make you do it, but seeing how this is our last time together and you're wearing your favorite panty girdle, maybe you could switch to giving me a blow job? Pretty please?"
It was interesting that I had not even thought of doing that all summer long or that Ted had ever mentioned that it was on his mind. I looked in Ted's eyes and saw the pleading look and I felt a thrill of excitement knowing I had this much power over him. "Sure Ted, I'm happy to do that for you. I've never done it before so you'll have to excuse my ineptitude."
"Greg you're the greatest and don't worry. I'm flying so high now, anything you do is going to be unbelievably fine!"
"So I guess I have to get on my hands and knees in front of you," I said, thinking out loud.
Ted spread his legs apart and I moved into position. His penis stood up at attention sligltly quivering. It was definitely going to be weird putting that in my mouth. Kneeling with my knees together I bent forward resting my forearms on Ted's naked thighs and fit my mouth over the top of his penis. The end was covered with precum whose taste I actually found to be kind of nice. It was an interesting consistency. Perhaps knowing that it had come up out of his body due to my previous work on his penis added to my attraction to it.
I don't know why I said it, but with the tip of his cock still in my mouth I said, "your penis is huge!" From the perspective of my mouth it certainly was. I heard Ted say, "thank you!" and in response his member seemed to grow stiffer in front of my eyes as if saluting me. I moved in again placing my mouth over the crest of his engorged member and closed my lips over the smooth surface. My tongue found the lower side of the tip and licked there. The result was almost to cause the penis to pop out of my mouth. I slid the penis further into my mouth to hold it down and now I began sucking on it in earnest.
As I sucked, my mind slid deeper and deeper into the sexual act I was performing and I lost awareness of my surroundings. My universe shrunk down to my determination to give pleasure to Ted's cock as it slid back and forth in my mouth. Eventually my hand found his balls and I played with them while sucking his shaft. Ted's excitement and sexual arousal continued to rise and finally after many minutes I heard Ted say, "have mercy on me, please finish me off!"
I quickened my pace pushing my face up and down on his penis. After some effort I felt Ted tensing up and it seemed like he stopped breathing. Then from deep down in his throat a sound emerged like a death rattle and Ted screamed, "oh God have mercy on me" and a torrent of hot cum came flying out of his penis into my mouth and throat.
When Ted's penis stopped pulsing I backed off slowly and sat back on my heels looking at the victim of my prowess. I debated what I should do with my mouthful of cum and then decided to just swallow it. A final present from Ted to me. Another trophy of our summer together. Almost tearfully I went back to Kate's bedroom and took off her pretty yellow dress and then her pink bra and panty girdle and put them back in the hamper along with the panties I had used in the bra cups.
When I returned to Ted's room he was still spreadeagled on the sofa. He looked up at me and shook his head. "What can I say Greg. I'm going to miss you."
I said, "I'll miss you too Ted." What I didn't say was how much I was also going to miss the yellow dress.
A few days layer Ted and Kate were all packed and ready to go to the airport. To my surprise Kate was wearing the yellow dress, the one and only time she had worn it all summer. She looked beautiful in it and I was jealous both of how pretty and feminine she looked, but also because she got the chance to wear the dress and I didn't.
I went with my mom and Phil to the airport and hugged Ted and Kate goodbye. There were a few tears here and there but plans were made for them to return the following summer, so there was something to look forward to.
A month later I came home from school one day to find that a package had arrived for me from Ted. It was a somewhat flat box. "What is that Greg?" my mom asked me.
On the outside of the box was written in several places "CD'S FRAGILE, DO NOT BEND." "I guess Ted has sent me some CD's."
Affixed to the outside of the box was an envelope that I opened. Inside was a note from Ted saying, "underneath the CD's is something that I salvaged from the Goodwill pile. Looking forward to next summer!" Ted.
"It's just some CD's that he no longer needs since he has them as MP3's."
"How sweet of him," my mom said.
"Yeah, I really like Ted. He's cool," I said.
I took the box up to my room and shut the door. Opening it I found a bunch of CD's resting over a piece of cardboard hiding what was underneath. I took out the cardboard and underneath was a manila envelope that contained something soft. I tore open the envelope and to my amazement saw that it was the yellow dress. I held the dress up to take a close look at it. An old friend that I thought I might never see again. I held the dress up to my body and looked in a mirror. I hugged the dress to my cheek and breathed in its beauty. I cried with delight. I imagined what was to come next summer.
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