Yellow Satin Has That Effect!
My new life began when I was 16. My father had been gone for 3 years, the victim of drunk driver, and now my family consisted of just me, my mom, and my two sisters, one 18 and one 14. As for me, my name is Mike, and I was a fairly skinny kid, about 5 foot 4 inches tall, and a diver on the Junior Varsity team.
I had been attracted to lingerie for a while because of the soft feminine flesh that it concealed in all the adverts. Me being a virgin, I could only dream of what those soft young bodies must feel like. Of course, a couple of girlie magazines let me know what they looked like, but…
Lately I had taken to jacking off in a pair of pilfered panties, while looking at the girlie magazines. My favorite picture was of a young looking blonde, giving a blowjob to a guy. There was this one close-up that showed his large cock just as it entered her lips, while she held on to the base of the guy's cock with pink painted fingernails.
I had sort of graduated from just jacking off with the panties, to wearing them, and sometimes I would get a slip out of the hamper and wear it too. I loved the slithery feeling of the nylon against nylon across my ass! This went on for a while, and then one evening, I "crossed the line."
It was a Thursday night, and my mom was playing bridge, and my sisters were out somewhere or another, and I had at least an hour or two to explore and play. I slipped into my older sister's room, and put on an old training bra, and a pair of her panties, and teased myself for an hour while looking at my favorite pics in the girlie mags. At first, I was fantasizing about how good it would feel if she was sucking my cock, and then slowly my fantasy changed to me doing the sucking! When I finally allowed myself to come, it was so violent that I almost fainted! I finally came to, washed my come out of the panties, and put them back into the hamper, put everything up, and put my own clothes back on. But I knew, this would happen again!
Over the next few months, I managed to snatch an hour here and there, but nothing like the time I wanted. I did, however, manage to get through all of my sister's and my mother's things, so I knew what they had, and where they were kept. I also found out that since I was so slender, darn near all of my sister's things would fit me, except for the shoes, but that with a bit of effort, I could wear my mom's shoes, and she had a bunch! Another plus on my side was the fact that all the guys on the diving team kept themselves shaved, even trimming the pubic patch as who wants a tuft of pubic hair sticking out of his Speedo? I also found out that Mom had some pretty sexy nightgowns, baby-dolls, and peignoirs hidden towards the back of her closet. She probably hadn't worn them since Dad passed away.
My time finally came around the end of June. My younger sister was away at a two week camp, and my mother and older sister were off on a week-long (maybe longer!) trip to look at colleges. This would leave lots of "girly time" for little ol me, who was being left alone, as I was the "man" of the house. Boy was Mom wrong!
I woke up early that first morning, with the whole day planned out in my mind in great detail. I pulled on a pair of shorts, ran downstairs and stuffed a bowl of cereal into my face, took the trash cans to the curb, and then rocketed back up the stairs to start my day, the girly way!
I had decided to start the way a real girl might start, with a bubble bath. First stop, though, was my Mom's closet, where I donned a white satin dressing gown, with lots of ribbon trim, and a sexy pair of high heeled slippers with feather trim. I almost came on the spot from the feeling of that gown, and my feet arched up into those rather low heels. Finally, after looking at myself in the mirror for a moment or two, I sashayed into the bathroom, where I drew a hot bath, lit a few candles, and poured in tome perfumed bubble bath. Warm water, soft candle light, perfume, and the sight of "my" gown and high-heeled slippers kept me in a state of excitement for the whole bath.
After my soak, I dried myself off, and used some perfumed body powder that matched the bubble bath, slipped on my dressing gown, and contemplated my options. Since I was home alone, no one was going to be coming by, and I had the time, I went for broke. I looked through my mother's things, then my older sister's, and finally, checked out my little sister's room, and there I found what I wanted. An almost full bottle of frosted, pale pink nail polish which seemed to have my name on it, was just sitting in her top drawer. With the help of an emory board, and about 2 hours of work, my fingernails, and my toenails were a sweet, girly pink.
Now, I had some more choices to make, mostly about color. Should I go with sophisticated and sexy black? Maybe I should opt for wanton red, or even virginal white? Then, it came to me. I almost danced into my sister's room, and went right to the bottom of her underwear drawer, past all the cotton, past the cutesy prints, past the couple of pieces of more risqué pieces, and went right to a pair of daffodil yellow, ribbon trimmed satin panties, and a matching soft cup bra that she had worn with a yellow gown in her position as a bridesmaid earlier in the spring. I shivered with excitement, as I slid off the dressing gown, and wiggled into the soft, silky panties. They fest so-o-o-o good as they slid up my legs! Then, I put the bra on backwards, spun it around, and got my arms through the straps. Even though my sister had small breasts, the B cups on the bra kinda sagged, but I wanted to feel my own nipples through the fabric, so I passed on padding. Then it was into the closet, the bag was all the way at the back, and I drew it out with trembling hands. I pulled the plastic off, and the dress just glowed. The dress was pale yellow satin, with a wide bright yellow sash and huge bow in the back. The skirt portion was a double layer of satin, and the sleeved were little caps, with a bit of white lace and a small yellow bow to match the sash. I remember my sister scoffing at how, "little girl" the dress looked when she wore it, but I thought then, and still thought, that is was the most feminine dress I had ever seen.
I slid that wonderful garment over my head, and even today, I can feel that soft cool fabric as it slid around my body. I just stood there, looking in the mirror. I didn't look exactly like a pretty girl, but I still couldn't tear my eyes from my image in the mirror. I made small turns, just loving the feeling of that material as swirled around my legs, just above my knees.
Now, with trembling knees, I made my way into my mother's room, and into her shoe collection. I had an idea of what I wanted, and within a few minutes, my eyes lit up with my discovery. I emerged from her walk-in closet with a pair of impossibly high, maybe 5 inch heeled white pumps, with a darling little ankle strap. I carefully laid them on Mom's bed, and began to look for stockings, but came up empty. The only stockings I could find were black, and everything else was pantyhose. Yuch!
With her shoes in my hands, I went back into my sister's room, and went through her things. The only think I could find was a pair socks. They were made of white nylon, and looked like the socks a little toddler girl would wear, with 3 layers of lacy ruffles around the top, and the whole thing ending just below the ankle. Well, I gave them a try. As I slid the little socks on, and then encased my feet in that white leather, I almost shot my load! I could barely hook the ankle straps without losing it!
I then began to struggle with the one problem that I hadn't foreseen. I could not pull up the zipper! I got it part way up, but couldn't figure out how to get it all the way to the top. As I stood there pondering the problem, I heard a voice from the bedroom door! I spun around as fast as I could in the heels, and there stood Tony, one of my best friends. Oh my God! I forgot to relock the door after I took out the trash! He was just staring at me, and calmly asked, "May I zip you up, Mike?" I just stood there and stammered, not knowing what to do. "It's okay," Tony said in a rush, "I saw the panties you were wearing a few weeks ago when you were swimming at my house. I picked up your jeans instead of mine, and when I reached in the pocket, I found your little pink panties." Again, all I could do was stammer, and then I started to tear up, actually beginning to cry a little. Without a word, Tony walked up to me, and took my shoulders in his strong hands. Tony had dropped out of high school in the tenth grade to work on cars, and we had gotten to be friends when I helped him get his GED, and he helped me work on the old Honda that I bought for $300. I hadn't realized just how strong he was, or how hot his hands were, or how weak my knees were. Again, without a word, he turned me around, and pulled the zipper of my dress up, and hooked the little catch at the top. Then, he turned me back around, and just looked at me. His green eyes were burning into mine, and I thought his hands would melt my arms! Not that I wanted to pull away, though. Images of all the pictures I had seen in girlie magazines flashed through my head, and my head was whirling with images, denials, anything and everything! "Mike," Tony began, and then stopped. He just leaned into me, and kissed me on the lips! So what did I do? I did the only thing I could do! I wrapped my arms around him, and kissed him back. He pulled me to him, and caressed my head, ran his hands up and down my back, and fondled my bottom though the triple layers of satin. We just stood there for what seemed like hours, exploring each other's mouths with our tongues, and holding on to each other like we were trying to keep from drowning.
As we stood there, one picture kept coming to my fevered mind. I could see that picture of the blond beauty with that gorgeous cock sliding into her mouth. I slipped down to my knees, and my fingers began to work all by themselves. I unbuttoned his jeans, and slid the zipper down. I then pulled the rough denim material down his legs, and was staring at a pair of black cotton briefs, containing a large, hard, twitching cock, I leaned into his crotch, and inhaled his slightly sweaty musk, and kissed his cock through the briefs. I heard Tony gasp, then sigh, so I knew I was on the right track. I could feel the straps of the bra, tight on my chest and back, the high heels arching my feet, and the satin of the dress as it fell across my calves. I watched my pink-painted fingers as they slowly caressed his bulge through the material, and then pull down his briefs to expose his beautiful, 7 inch cock, right in front of my lips! I didn't need to even think. I kissed the tip of his cock, and then began to slip it into my hungry mouth. I was clumsy at first, but guided by Tony's gasps, sighs, moans, and encouragement, I got better, fast. I finally got his cock all the way into my mouth, and began to suck it in and out of my mouth, while I played with his balls, and squeezed his ass cheeks. When he came, it was hard, hot and salty, and I lovingly swallowed all that I could, and then licked up the rest. As I knelt there, licking his soft penis like a lollipop, I knew I had made a far-reaching choice.
Tony took my shoulders again, and slowly lifted me to my feet, and kissed me, hard. "You are the most beautiful girl I have even been with," he sighed. "But I'm not a girl, and I'm not beautiful," I almost sobbed! I was now very horny, and very, very confused! "You are to me," he answered, holding me close." All you need is a little lipstick, maybe a wig, and some jewelry, and you're going to be perfect.
With that, he detached himself from me, and pulled his jeans, underwear, and trainers off, and then unzipped my dress, and helped my get it off, and on to the hanger. Then, with him in a black T-shirt, and me in yellow satin panties and bra, girly socks and high heels, he picked me up, and laid me on my sister's bed, Then, he removed his shirt, and got in beside me. We kissed some more, and then his hand moved to my panty covered hard-on. He asked me to masturbate for him, while he held me. He told me that he would work up the nerve to return the favor of the blowjob, but it might take a little while. I began to work on my cock, as he began to kiss me, and grab and tweak my nipples through the bra. Finally, he pulled the bra cups up, and took my breasts in his mouth, swirling his tongue around my nipples, and gently biting them. I came hard when he started that! Tony gently scooped up some of my cum, and gently fed it to me. I not only ate it willingly, but I sucked his fingers clean.
We decided to go down to the kitchen to get something to drink and to talk, after checking to see that the miniblinds were closed. Well, after an hour of talking, with me in my bra and panties, and back into my dressing gown, and him in just his jeans, we decided that the next step was obvious. But, after several attempts, Tony just could not get his cock to penetrate my virgin asshole. Finally, Tony looked at the clock, and told me that he had to go, but as the next day was Sunday, he would be back, with a few surprises for his new girl. "By the way," he said as he left, "I can't call you Mike when you are dressed like this, and I'm making love to you. Could I call you Michelle?" Michelle, I thought, Michelle. What a lovely name! "Of course, sweetheart," I heard myself say in a high soft voice. "Michelle will be waiting for you tomorrow!"
That night, I could barely sleep! I had taken what I thought was a small step, and it ended up as a marathon run! I had dressed as a girl, kissed a boy, man really, and given him a blowjob! Then, even though it was unsuccessful, I let him try to fuck me up the ass! I finally fell asleep in one of my Mom's baby-doll nightie, and dreamed some very erotic dreams!
The next day, at around 9:00, the doorbell rang. I had locked the door, this time. I looked out the window, to see Tony standing there with a box, and a couple of bags. I opened the door, using it to shield the neighborhood's view of me in a pale pink baby-doll and high heeled slippers. Tony slipped in, and after I locked the door, he grabbed me and kissed me like there was no tomorrow. I melted in his arms, and felt like I had died and gone to heaven! He finally broke his lip lock, and led me upstairs. From a small bag, he took a tube of something, and…then I recognized it. It was a pink rubber butt plug! It was about 4 inches long, and about an inch thick, tapered at the front, and the back, ending in a flat piece that would keep it from sliding all the way into someone's ass. The tube, I saw then, was KY Jelly. Tony explained, while he held me on the bed, and caressed my nipples and ass, that if I wanted him to, he would use the plug to loosen me up, and when it felt right, we could finish what we started. He didn't have to ask me twice! Soon, his cock was back in my mouth, and this time, he held my head and actively fucked my mouth. Again, I swallowed his load of cum, and again, I licked up the remaining cream, licking his balls, and moving back to kiss his thighs and ass. He pulled me up to him, and gently kissed me, then started kissing me on the face, the neck, and the chest, paying special attention to my very sensitive nipples. Finally he worked his way down to my panty covered cock, and began stroking my cock. He finally pulled it free of my frillies, but left my balls trapped by the material. He took me in his mouth, and within a very short time, I was shooting my load into his mouth. He slid back up, and then kissed me, sharing my cum with me, as we swirled it around in our mouths. Then he told me to get on me hands and knees, and he got out of bed. I felt the bed heave again as he got back in, and then something cool was being applied to my ass. His finger slipped into my hole, and he held it still for a moment, allowing me to get used to the feeling. Then he began moving it in and out. I began bucking against his finger, and he pulled out. I was disappointed, but soon felt the tip of the butt plug against my virgin hole. He started to push it in, but it hurt so much, that I pulled away.
"Do you want to do this, Michelle?" he asked softly. "I do, but I'm scared!" I answered back. "Well, I have a little fetish that could help us do this," he said. Are you willing to try? He explained what he wanted to do, and I agreed, a little reluctantly. At this, he rolled me onto my back, and took out a pair of what I learned were Velcro hand and ankle cuffs. He wrapped one around each wrist, and then tied them to the headboard. My ankles now got a cuff each, but he did not tie them to the bed. He took a thick wooden dowel rod, about 3 foot long, out of his box of tricks. "I saw this in a movie once, and it really, really turned me on," he explained, as he hooked an eyebolt at each end into the cuffs, holding my legs apart. Finally, he brought out a rubber ball with a strap passing though it, and gently put it in my mouth, buckling the strap behind my head. I was tied up and gagged, and was as excited as I had ever been! Next, he took the bar, and raised my legs up over my head, and put more lube in my asshole. Then, without any warning, hi began to work the plug up my ass. I yelled into my plug, and began to cry with the pain. Finally, when I thought that my whole body would be split in two, I felt a pop. And the plug was in. Tony lowered my legs, and began to kiss my face, and bite my nipples through the lacy fabric of my nightie. I relaxed, and the pain level lowered until I started to be excited again. He again began to suck my cock, and I came again. The plug was no longer an alien intruder, it was a new friend!
Tony took off the gag, but left me bound, as we snuggled and kissed for a while. Finally he released me, and I pulled my panties and shoes one, and we went back to the kitchen for a snack. As I sat on the hard wooden chair, I could feel the plug being pushed into me, and as I swayed on my heels, it worked its magic on my ass.
Back upstairs, Tony put me back into bondage, lifted my legs, and pulled out the plug. The feeling was complete emptiness! Not to worry, though, as he brought out a large pink, realistically shaped dildo. He slowly worked this in and out of my ass, until the pain went away, and, and was replaced by extreme pleasure!
Tony then put the butt plug back in, but this time is was a larger one, and while it didn't slip in easily, it was far easier than the first one. Again I was let out of bondage, and Tony told me to take a bath, and he would give me the rest of my surprise. I got a bubble bath, without removing the new plug, and heard Tony taking a shower in the spare bathroom. When I finished, I slipped on my heels and dressing gown again, and went back in to find my surprise. There, on the bed, was a corset! A beautiful, pink satin corset, with matching panties, and a pair of white stockings with large white bows on the back of the ankles were laying out on the bed. "Oh Tony," I sighed, "That is the most beautiful, feminine thing I have ever seen! He picked up the panties, and I shed my gown as he held the panties for me to step into. After they were up around my hips, he picked up the stockings, and rolled them up my legs. I felt like a princess! Finally, he told me to stand up, and hang on to the dresser, as he wrapped the corset around my waist, and then began tightening the laces. When they were so tight that I almost couldn't breathe, he told me to take a deep breath, and tugged it a little tighter! As he tied the laced, I looked in the mirror, and saw a girl's body, and a boy's face. That changed in a moment, as Tony threaded the straps under my panties, and hooked them to my stockings, and buckled the white pumps back onto my feet. He then reached into the box and pulled out a blonde wig, done in a sort of longish pageboy cut. He explained that it was his Aunt's, and she had left it at their house when she went home last week. I applied a little pink lipstick, and soon a girl was looking back at me, not me! The corset had even given me little boobs, as the flesh was bunched up above the stiff garment.
We kissed again, and then he asked me if I was ready to go all the way. I nodded, and asked him to tie me back up, so I couldn't resist. I gleam came into his eyes, and very, very soon, I found myself gagged and bound, with a naked man kneeling between my spread legs. He had shoved several pillows under my ass, so I was completely vulnerable to his cock.
Slowly, he spread some KY on his cock, and then on and in my asshole. Then, he began to ease his hard cock into my ass. It was thick, hard, hot, and hurt so bad! I was sobbing into my gag, but my cock was hard as a proverbial rock! He finally got that monster into me and held still for a moment. Then, he began fucking me like woman. He would pull that gorgeous cock almost out of me, and then slam it back to the hilt, slapping his balls off my ass, while my own cock bobbed around, with no relief in sight. With a grunt, he blew his load into my ass, and I could feel his cock deflate. It was the saddest feeling in the world.
Needless to say, we spent the whole week exploring our new relationship. We were friends the week before, and now we were lovers. In fact, I was in love with Tony. I was afraid to voice this to him for a long time, but when I did, well, that's the NEXT story!
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