A Tranny Honeymoon with Mom

I could not believe my sister Sara was getting married. She was a beautiful woman, with long shapely legs, firm breasts and a tight ass, but she was also a bit of a slut. Put a couple of drinks in her and you were sure to get lucky. I should know, because I was her younger brother, and I had known her intimately since I hit puberty. I had started my trip to manhood when I first got hard and horny noticing her lovely body. The first time I jerked off I was staring at her photos on the computer which left nothing to the imagination. She really should use passwords, but I'm not complaining since all her intimate secrets were revealed to me. The photos which drove me crazy were her deep throating her numerous boyfriends. She was an expert cock sucker and enjoyed swallowing cum from what I could see in the pictures. She also used numerous dildos and butt plugs, oh my. I had to check out her bedroom, and the weekend my I was left alone was my introduction to womanhood.

The Friday night after my mother and sister went out of town finally arrived. I went in to my sisters' bedroom and shook with excitement. I could smell her perfume and her bed looked so inviting. I carefully looked in her dresser and enjoyed touching her bras and panties and nylons. My dick was becoming so hard and my hands were shaking. I removed my clothes and stared at my hard-on leaking precum. I took out a pair of pink, frilly panties and held them to my face. I could not help myself as I held them over my face and sniffed them. The heady odor was spectacular and my dick was throbbing. There was no turning back as I slid the panties on to my legs and pulled them tight across my hot cock. Fortunately I was smaller than my sister so the panties fit okay. I looked in her dresser and removed a garter belt and two black nylons stockings. Was I brave enough to try them on? I felt the sheer nylons and ran them along my arm and felt all tingly inside. Then I carefully took a nylon and folded it up and started to roll it up my leg. I did the same with he other one and put on the garter belt with shaking hands. This was the best thing I ever experienced and I wanted to keep going. I found a black bra and attached it, and stuffed the cups with more of her panties. I looked in the mirror and my dick poked up from the panties and I could not help stroking it and caressing my nylon covered legs with my other hand. I took her water glass from the dresser and rubbed my dick until I started to spurt cum in to the glass as I kept striking and cumming. I lay on the bed feeling spent and took a nap.

I woke up four hours later feeling refreshed. I needed a shower, and I decided then and there to shave my legs and chest after cracking open a bottle of my sisters vodka. I got a little drunk and a little horny as I sat naked on sis' bed. Her makeup table was next to the bed, and she had a marvelous collection of cosmetics and perfume. I spent some time putting on makeup, and struggled with the mascara. I put her lipstick on my lips and could not believe how much I looked like Sara. I went and got my camera and took photos of my every move. I found a pair of white panties and put them on. Next I put on sheer nylons and I stared at my smooth, shapely legs and marveled at how silky they felt on my legs. I slipped on her push up bra and stuffed it with her panties. In her closet was a red dress which I had loved to see her in, since it was tight on her ass and short on her legs. I squeezed in to it and put on her red high heeled shoes. Damn, they must be six inches tall as I tried to walk in the painful things. I looked at my reflection but it still wasn't complete. I went in to my moms' bedroom and found her red headed wig. I used some of moms best perfume and went back to my sisters bedroom and admired myself in her mirror. I had to admit I made a stunning redhead, and was totally convincing except for the big dick poking through the front of the red dress. I took the glass and began to stroke my hard-on and soon gasped and moaned as I unloaded my spunk in to the glass. After wards I stared at the creamy liquid in the glass. I could not resist sniffing it, and a little bit of cum stuck to my nose. I wiped it off with my finger, and stuck my finger in my mouth. It was a unique taste, not repulsive like I thought it would be. I took a swig of vodka and then drank down the glass of cum. The rest of the weekend was spent trying on all my sisters' pretty things, as well as some of moms.

The next few weeks went by in a blur, except for when I tried my sisters toys. I started off using her dildos using the small ones with lots of lube. The first time that I came in her panties just from stimulating my prostate was unbelievable. I soon tried a butt plug and found it a thrill. My favorite was a fairly large black butt plug with a battery powered vibrator. I had to first loosen up my asshole with lube, and work in progressively larger toys. Finally I could get the tip of the butt plug in and slowly work it in while wearing her sexy lingerie and looking at porn videos. To get the largest part of the plug in took time and brute strength. But what a feeling it was to have the plug fill up my asshole and tickle my prostate as it vibrated and I moved my body in her high heeled shoes. I would stick my legs in to her headboard as I stared at my cock just inches from my mouth. Then I would stroke my cock and shiver and shake when I finally shot a hot load of cum in to my face. Taking out the jammed in butt plug was a difficult and short term painful affair.

Anyway, my sister was getting married and had bought a gorgeous Wedding Gown. The dress was white, of course, and had a long train and long veil. My sister kept it in her room and

I could not get near it. Finally, the night of the Jack and Jill arrived and I faked an illness in order to stay home and play. As soon as the house was empty I went in to my sisters' room to get it on. I poured out a drink or two as I made up my face. Sis had a white corset, white garter belt and white nylon stockings which I carefully put on. I slipped on a pair long white gloves and stepped in to the Wedding Gown. It was a struggle to get in to this thing but I finally got it on. The back was fastened with these buttons and loops and I managed to get a couple at the top done up. I put on the red wig and the veil on top of that. I slipped my feet in to these silky white high heels and had tears in my eyes as I looked in the mirror. I could never experience wearing a Wedding Dress in public but this was the next best thing. I slowly walked in the outfit trying not to trip in the gown on the precarious high heels, and being a little drunk did not help. I needed photos so I took my camera and tripod in to the large back yard. I must have taken thirty pictures in between drinks and touching myself. Finally I cautiously moved back in to the house and heard the a car outside.

I stumbled up the stairs as quickly as I could and went in to my bedroom as I closed the door. I heard the front door open and voices could be heard. Oh, no, I was going to be found dressed like a girl wearing my sisters clothes! I was scared and shaking in my heels, but also slightly aroused and very excited. My dick was straining in my panties and I rubbed my legs together and became even more aroused. I heard noises on the stairs and opened my door a little and saw my mother being carried in to her bedroom by my sisters' fiance. He laid her on her bed and just stared at her, then he unzipped his pants and stroked off while staring at mom. Then he finally left the house. Curiosity got the better of me so I silently entered my moms' bedroom. She was wearing her new black sparkly dress which had ridden up showing the white skin above her sheer black nylons. Her long, shapely legs were fantastic to look at, and I moved closer and could hear her snoring. Its funny, but I had never thought of my mom as a sensual thing, she was just mom: but looking at her lying on her bed I saw how pretty her face was, and how her body looked curvy in her tight dress, and how her perfume was enticing. Wearing a Wedding Gown while dressed as a girl in front of my passed out mom was a thrill as well. It was wrong, but I wondered if I should take this further and take advantage of my mom in her condition. I wanted to leave and I left her bedroom and closed her door and turned out the light. I went to my sisters room and removed her Wedding Gown and the rest of her things. I was naked and could not stop thinking of my beautiful mom, vulnerable and alone on her bed.

I finally gave in to temptation, and promised myself I would only go in her room and try on her things and take some photos. I went back to her bedroom and approached my mothers' bed. She had rolled over and I could see her ass cheeks in her small blue panties. My cock was fully erect as I stared at her lovely shape. I went to her dresser and removed a similar pair of panties and put them on over my leaking cock. Moms' nylons and garter belt were next and the nylons felt wonderful as I pulled them up my legs. She had a low cut bra that I put on as I looked at her lovely sleeping form. I approached her and thought that it would be okay if I jacked off as long as I did nothing else. I got on the bed next to my passed out mom and just stared at her as I imagined making out with her. I suppose that as long as I did not go all the way, I would not be a low down motherfucker. Suddenly, she rolled over and I was face to face with her and her breasts were pressed in to my chest. Mom was making sounds as she pressed her body in to mine. I could feel her nylon covered legs rubbing in to mine and it was incredible. Now I don't know about you, but this was not a time to be timid, if she woke up I would gladly face the consequences.

I looked at my moms' pretty face, and her lovely lips and I kissed her! The sky did not fall, lightning did not occur and the world did not end. Even more exciting was the fact that mom responded by pressing her body even more tightly in to mine. I kept kissing her and ran my hand along her lovely ass over her panties which were now wet. I lifted her panties and ran my fingers over her glorious cunt. She was moaning and getting wetter as I slowly inserted a finger in to her wet pussy. My dick was throbbing as I fingered my mom and stuck my tongue in to her mouth. We kissed for quite a while, and then she rolled over again, this time on top of me. I sniffed my finger and then could not resist sticking it in my mouth tasting my moms' essence. I was close to exploding as I felt her breasts on my chest and my legs humping hers. I was dry humping her as I inhaled her scent and our lips met again. I was at the point of no return now, as my body shuddered, and she twitched, and we both came at the same time in to our panties. I reluctantly left moms' bed and put away her lingerie and quietly left her room as she slept soundly. I was proud of the fact that I had not fucked her, but I also regretted it as well. Luckily for me she did not remember anything that happened that night and sis's wedding took place with her wearing her pretty Wedding Gown.