Dressing Up In His Mom's Clothes

Summary - Jeff and I explored sexually, and when I wore his mom's clothes, I truly felt like his girlfriend, experiencing a deeper connection that blurred the lines between fantasy and reality.

His name was Jeff and I met him about a year ago when he first moved into my subdivision.

He was 14 and was in the ninth grade. I was 13 and only in eighth grade, so I looked up to Jeff.

He was not a jock but he was not a nerd like me. He was about eight inches taller than me and outweighed me by about 30 pounds.

So I was almost more like a little sidekick for him than a true best friend.

All my life I have always been friends with kids who were older than me. I guess you could say I was more of a follower. I think the only reason that he let me hang around with him was that I was the only kid in the subdivision who was even close to his age.

We started to experiment with sex after we were friends for a month or so. His dad worked in a sales job that would take him away from the house for weeks, and his mom worked the second shift so he was home alone from the time we got off the school bus till his mom got home at 11:00 at night.

I would go over to his house after supper and hang out till I had to go home.

It was one night that I was over that he got out some of his dad's playboys and we sat down and looked at them.

Like most kids our age we ended up masturbating together by the end of the night. He had an easygoing way about him that made me very comfortable about experimenting with sex.

One time when we were in the middle of one of our group masturbation sessions, without warning he moved over close to me and pushed my hands off my cock and grabbed it with his hands, and started to stroke it. I gave him a puzzled look but all he said was, "You go too fast, let me show you how to do it".

His hands were much larger and a little rougher so it felt a little different than when I did it. He did not stroke my cock fast and short like I did. He would do long, slow more powerful strokes.

I did not come in a fast short climax like I did when I stroked myself. He slowly worked me into a deep long climax.

I was moaning and whimpering and squirming all over the place as he got me closer and closer to my climax.

I looked at him as he was doing it and he looked like he owned me or was controlling me. The strange thing is that I liked it.

I liked the fact that I was giving control to him. He would make me cum when he was ready for me to cum! As I got closer to cumming he sped up and started to say things like" That's it cum, you're doing it, shoot your load".

I liked the encouragement and I wanted to make him proud of me and do a big load. When I did cum it seemed like a gallon and Jeff pointed my cock so it covered my chest and face with four or five spurts.

I knew that now things had changed between us. We were no longer two kids masturbating, we were stating to experiment with gay sex.

Over the next few weeks, we did a lot of experimenting sexually almost every night at his house. We would masturbate each other till we came to explosive climaxes.

He seemed to like to make me cum more than I did doing it to him. He liked to control the pace and make me wait as long as he wanted, then finish me off with a mind-blowing orgasm.

When I did him it was more like I was following his commands.

He would tell me how fast and when to finish him off. I could tell that these were not his first experiences like they were with me.

One night he did tell me how in his old subdivision he had a friend that was my age who had a long history of sexual experimentation.

He explained that he was bisexual and liked guys and girls.

He told me about his girlfriend Sandy he had been having sex with for a while now. He said he liked her but she did not enjoy experimenting with sex as much as he did. He told me how she had even balked at oral sex now because she said she did not like it at all.

"Maybe you could be my girl," he said in a joking manner as he rubbed the top of my head. The way he laughed I did not think much of it.

He was joking, I tried to tell myself. But in the back of my mind, I had a feeling that I was to find out what he had in mind.

A few weeks later I was at his house on a Friday night when both his parents were gone. My parents gave me the OK to sleep over for the night.

Because we had a little more freedom he talked me into raiding his Dad's liquor cabinet and we both had a few shots of whiskey in Coke.

It was my first time drinking and it hit me pretty hard.

It was not Jeff¡sfirst time and it seemed to have almost no effect on him.

We got out his dad's Playboys and started to masturbate. The drinking seemed to make me even more horny than I was usually when we masturbated.

I was just getting started when Jeff came over and grabbed me. He pulled me over to the couch and sat me down on it. In my drunken state, I was like a rag doll as he moved me to his liking.

He pulled out his cock and I grabbed it and started to stroke it. I instantly felt very passive with me sitting and him standing over me. I was so drunk that tried to lean closer to get more coverage.

As I was moving I slipped a little and found my face very close to his cock And that's when it happened. It was all so fast that I had no time to think.

Before I knew what hit me I felt his one hand on the back of my head as the other hand was guiding his cock into my mouth.

He had misinterpreted my slip as an invitation to use my mouth like he would his girlfriends. My slow protest of " no " had only made it easier for him to invade my mouth by unlocking my lips and forming them into a perfect "o".

I put up a little fight but his cock was all the way in my mouth like a gag. While one hand held the back of my head very tight so as not to let his cock out of my mouth, the other hand had a fist full of my hair and was moving my mouth up and down on his cock. I think that he was so hot and horny that he never knew that he was raping my mouth.

It was his constant encouragement that made me succumb to my fate.

Baby your mouth is so hot, God your lips are soft, and you suck cock just like a girl. I think the last one."

You suck cock like a girl is what got me most turned on. I started to think of myself like his girlfriend and I wanted to take the role of the submissive one in this relationship.

I wanted to make him proud of me and I wanted to bring him pleasure. When he was close to cuming he finally released my head from his grip and let me work his cock myself as he leaned his head back and closed his eyes.

I put one of my hands on the base of his cock to hold it and the other hand on his ass for leverage and then went nuts on his cock.

I had his cock going in and out of my mouth like a piston on a sports car. When he let out his final moan he grabbed hard on the back of my head again and forced all of his cock in my mouth and some of his balls as he started to cum.

I think his cock was so far down my throat that I did not even have to swallow.

I started to feel myself blackout from not being able to breathe, and from wanting to gag because his cock was forced so far down my throat. But right before I was about to pass out he let me head loose.

At I same time without even thinking about it I grabbed my cock and started to stroke it. I think it was only two or three strokes as I shot the biggest load of my life all over my belly and face.

What was different was that I didn't let out a low moan like Jeff. I let out a very high pitchy whimper as I shot my cum all over myself.

As Jeff looked down at me covered in my own cum, and some of his on my lips, still have dazed from almost passing out and coming at the same time.

He gently stroked my hair and said "That's a girl, that's a good girl".

After that day I was always the very passive one in the relationship with Jeff.

I would suck him off almost every day after school, then most of the time would masturbate while sucking his cock, or I would jack off in front of him after he would cum in my mouth.

He seemed to like to watch me stroke my cock like a madman till I would shoot all over myself. And it would turn me on to perform for him. One time when we pulled out his dad's playboys we found a few hard-core books in the same drawer.

The books had more action pictures of intercourse and oral sex and one magazine that was just anal sex.

The one magazine that Jeff could not put down was a bondage monthly.

It was full of women tied over chairs, hogtied lying on floors, and tied up and hanging from ceilings.

When Jeff was ready for his blow-job that day he removed his belt and before I knew it he had me on my knees with my arms tied behind my back and wrapped around a bar stool his parents had in their rec room bar.

My moth was about the height of the cushion, so it was perfect for Jeff to use it, like he so loved to do.

It was my first experience with bondage and I loved it. I loved the way it made the already passive and humiliating act of sucking his cock even more exciting. As I looked up at Jeff I could also tell it was more exciting for him to see me tied and helpless as he slowly feed me his cock.

When he would bottom out his cock at the back of my throat I would fight my restraints a little as I would gag. I could see it was turned on for him for me to fight my restraints, so I started to play the part of a helpless bound victim. I started to whimper and cry a little as he was feeding me his cock.

As I was pulling on the belt that was holding my hands behind me. He started talking dominantly to me, calling me his little mouth slut and a little fag cock sucker.

When he was getting close to cumin he grabbed the back of the bar stool so my head was forced in his crotch so that all his cock was rammed down my throat.

I loved the feeling of being tied and to have no choice but to take all his cum.

We experimented with more bondage on and off for a few weeks and we both seemed to love our roles. It was on a day we had off of school and his mom was going to be gone all morning that we were in his basement rec room that the most exciting thing happened in my relationship with Jeff.

He was sitting on the floor looking at one of his dad's sex books, and as was usual now, I was laying between his legs with his cock in my mouth.

He got a funny look on his face as he told me to stop sucking him. I looked at him and said, "What's up Jeff ".

He looked over at the corner of the room where there were a few baskets of laundry that were waiting to be folded. "If we are going to do this, let's do it right," he said in a loud-dominate tone as he walked over to the baskets.

He went through the clothes and pulled out some of his mom's stuff and tossed it to the side. "Put this on I'll be back in a minute, I have to get a few more things". I slowly walked over to the pile to see what he had selected for me. On the floor, I saw a bra, panties, pantyhose, a slip, and a dress. I think the thing that surprised me more than anything is that I did not even have a second thought about dressing in his mom's clothes. I was pulling a pair of black satin panties with lace trim up my legs before Jeff was out the door.

I put the matching bra around my chest backward and snapped it first, then pulled the snap to the back, and then slipped my arms through the straps like I had seen my sister do a million times.

I loved to peek in her room as she got dressed when I was younger. I loved the feel of the nude-colored pantyhose as I pulled them up my legs, but the best part was how the slip felt on my legs as I dropped it over my head.

I picked up the dress and opened it up and stepped into it and slowly pulled it up and put my arms in the long sleeves.

It was a mauve-colored satin dress that I had seen his mom wear when she went out for the night with Jeff's dad on Saturday nights. I felt the dress get very tight on me and I realized it was Jeff pulling the zipper up in the back. " not bad baby" Jeff said to me as he gave me a hard slap on my ass.

"Here put these on, " he said as he handed me a pair of his mom's shoes.

They were a pair of high-heel pumps that matched the color of the dress. As I slipped the shoes over my nylon-covered feet, I noticed that my legs looked very hot in the hose. I have light-colored hair so the little bit of hair I have on my legs did not show.

As I slipped on the last shoe I felt Jeff pull my hair as he quickly pulled it back into a ponytail and wrapped a satin hair wrap that also matched the color of the dress.

As he pulled my hair back, I first saw my image in the mirror behind his dad's bar. I was a little shocked at how sexy I really looked. His mom is short for a woman so her clothes did fit me very well.

I did not look 100% like a woman, but I looked like a young feminine guy decked out in a sexy outfit. As I was looking at myself I started to feel my cock now trapped in satin panties start to grow with excitement.

Before I could enjoy myself I felt Jeff's hand on my back as pushed me over a bar stool. " we aren't done yet babe" Jeff said as he went back to the bag he had brought down with him.

He pulled out a pair of handcuffs and some short lengths of nylon rope. I guess Jeff's mom and dad were also experimenting with bondage. In a short time, he had me tied spread eagle over the stool so my feet were off the ground and my hands were pulled so far over that my crouch rested on the top of the cushion.

How can Isuck his cock with my head pulled so far over I thought to myself.

Looking down at the floor I saw the magazine that Jeff was looking at when I was sucking his cock. It was not the Bondage monthly magazine that Jeff always read and got most of his ideas from, it was the magazine that was full of anal sex pictures.

Jeff was going to fuck my ass with me decked out in his mom's clothes looking like one of the girls in the magazine getting pounded up the ass by some large muscle-bound stud.

When I opened my mouth to protest I was rewarded with a large red ballgag that rammed in my mouth and strapped behind my head.

When Jeff saw me looking at his magazine he knew that I had finally understood my fate."

I thought you might put up a fight that's why I tied you down first," he said as he lifted up my dress with one hand and started to slap me with his other hand.

As hard as I tried I could only move an inch or two as he slap my butt 15 or 20 times.

These were not soft slaps. Jeff was raising his hand as high as he could and coming down full force on my nylon-covered butt.

When hefinely stopped I was whimpering and crying and wiggling as I tried to recover from the beating." I thought you needed your ass warmed up a little before I fuck it, babe," Jeff said as he pulled my hose and panties down to expose my red butt.

He reached into the bag and pulled out a jar of Vaseline and started to cover his cock with it as he inserted two oiled fingers in my ass to get me ready. What surprised me was that Jeff did not just ram his cock in my ass and give me a fast rough fuck. He put his cock on my virgin hole and then inserted only a little at a time and then backed out.

As he was doing this he would stroke my nylon-covered legs and tell me what a sexy girl I was and how hot I was making him.

He was treating me gently like he would a real girl, and I loved it.

He did this for about 5 minutes till I wastotally relaxed and then he pushed the head of his cock past my anal ring.

Once the cock was past the ring the pain was not as bad, and I was starting to enjoy it a little.

It don't know why but it felt fulfilling to have mass full and it made my cock grow in my panties.

When his cock was all the way in my ass he laid his chest on my back and still stroked my legs but with his other hand he found one of my satin-covered nipples in my bra and started to play with it. biting my ear lobe he kept on talking to me asking me if I liked being his girlfriend and telling me I was his girl now because he was my man to take my virgin ass hole.

All I could do was moan in my ball gag as he was taking me to such a new level sexually. But dressed like I was, and in the position that he had me, I think it was more than a sexual feeling. I think I was beginning to fall in love with Jeff.

He had shown and taught me so much about myself that I felt so indebted to him. I wanted to give all myself to him. I would never say no to any of his needs.

He slowly started to pull his cock out and I felt it leave but he slowly worked it back in. It was painful as it passed my ass hole ring each time.

But after a while, as he slowly started to speed it up a little I could feel my ass stay open a little. It was not painful as the head of his cock passed in and out of my ass.

This is when I really started to feel the pleasure of being fucked. I started to wiggle in my restraints and moan into my gag as I was getting more and more excited. Jeff could feel my heightened excitement and this made him speed up even more.

He grabbed my hips for leverage and started to give me all that he had. I was getting so hot from his cock going in and out ass, but I was also excited by the feel of my satin-covered cock being rubbed back and forth on the top of the cushion. He was rubbing my cock to a climax on the cushion.

I felt it slowly coming from deep inside me. It was not like the orgasms when I masturbated. It was not coming just from my crouch. I felt it in my whole body. It was coming from my ass, from my balls, from my cock, and from every pore of my satin-covered body.

Jeff was ready to cum also and in his heightened excitement he grabbed one of my shoulders with one hand and with the other hand he grabbed my ponytail. With his hand on my shoulder, he pushed me back towards him at the same time that he rammed all his cock in my ass.

He let out a loud moan at the same time that he pulled as hard as he could on my ponytail. This caused my head to pull backward and my back to arched high in a very feminine and sexy way.

It also caused my cock to rub the full length of the stool cushion, which made me cum in very long slow spurts.

As I felt his cum filling my ass I also felt the cum filling my panties and creating a giant wet spot in the front of my dress. I let out a high pitch whimper and moan as the final spurt of cum filled my panties.

Jeff was so excited that he was still ramming his cock in and out of my wet and dripping cum filled ass.

He still was pulling on my ponytail when I finally opened my eyes coming out of my sexual high. And that's when I saw her.

Jeff's mom standing in the doorway of the room. With both her hands over her mouth, she said in a loud scream, "Oh my god".

And here I was dressed in her clothes with a large cum stain on the front, and her son was so excited that he did not hear her scream and was still pounding my ass hole with a frenzy.

As I looked at the horror in her face as she looked at me I knew she thought I was very sick in the head for what I was having done to me and the way I was dressed.

But I knew that this would not be the last time that I crossdressed, and it would not be the last time I gave myself to a man when dressed. I knew that I had found my life purpose, to bring pleasure to men, and at the same time pleasure myself.