Well it had been one of those days when all that could go wrong did. I was about an hour from getting off and called Corky, my girlfreind to let her know that i was running late. Well why would the day change. She let me know that she got called into work and she was about to leave. Great another boring evening at home. We chatted for about 10 minutes she listen to me rant about my crappy day. We were saying our good-bys when Corky told me "dont worry your day will get better" thinking to myself yeah right...
Corky and I have been togther for about 10 years -- we were 15 when we met and I had always tryed to be as open with her as I could. I had told her that I loved womans panties, lingerie and clothing in. She endulged me by letting me wear and often buying me panties. I always tryed to hint I wanted to explore more then just panties but when I tryed to push the subject she shyed away.
I got home about 6:15 there was a note from Corky that she would be home about midnight, take a shower, relax and enjoy what she had laid out for me. I didn't understand what she ment untill I walked into our room.
There laying on the bed was a satin pale pink teddy with white lace, a pair of pink silk hose. In that moment all my days troubles were out of my mind. Was I dreaming? Did she really lay this out for me? Was this what she was going to wear when she got home, my mind was racing.
I headed off to the shower when I opened the shower door there was a razor, cream and another note. I picked up the note " I want you to shave so that all of your skin is as smooth as the satin teddy I laid out for you" Who was I to argue, I went to work , slowly shaved my legs moving up to my pubic area I shave myself a cute little triangle patch, shaved my balls. I shaved my chest, which wasn't to hard seeing how I dont have much hair there anyways, then finished off doing my underarms.
Heading back to the bedroom it was all could do not to go jack off I was so horny, but I knew I should wait. I slowly slid into the teddy as the satin touched my cleanly shaven body the sensation was heavenly. I slid the stocking up one leg then the other, I thaught I was going to explode right there, I took some deep breaths and tryed to relax. Easier said then done.
I put my robe on and headed to the kitchen to have dinner & try to calm down but as my body moved and rubbed against the satin it made it hard to think about anything but sex. I went ahead and made something to eat and went to the living room to watch TV and have my dinner.
About 10 Corkey called and said " I'll be home in a couple hours , why dont you go to bed I'll wake you when i get home." I wanted to ask her about the outfit she left out for me and all she would say was that she hoped I liked it and we would talk more about it when she got home. I headed off to bed with millions of thaughts running thru my head. I layed there for a while slowly drifting in & out.
I didn't wake to her coming into the house or even into the room. I didnt wake up tell I heard the shower. I rolled over and fell back asleep while she showered. She climbed into our bed slowly cuddling up next to me. I awoke to her slowly sliding her hand on my leg, I laid there enjoying the touch of her against the silk hose. She slowly worked her way up to the leg opening on my teddy sliding one hand under the satin around the curves of the leg opening around to the front letting one finger slid down my shaft that was wide awake. I tryed to roll over but she stopped me telling me just enjoy. She slid her hand down over the satin that was on my ass, then moving her hand back up the center of my ass stopping and making circles on the satin right on my asshole, I could feel the precum dripping from me while she circled.
She stopped for a moment and slowly rolled me onto my back thats when I saw she was wearing a jet black nightgown. I started to wisper to her and was told "shhhhhhhhhh enjoy". She started to rub my nipples thru my teddy then she moved the teddy just enough to take my nipple into her mouth. Sucking, flicking and nibbling on it moving from one to the other, reaching down to stroke my cock thru the satin. I know i had a wet spot forming. She quit stroking my shaft and spread my legs a little apart, moving her hand down to my balls then further down again she started to run circles around my ass. She unsnapped the teddy releasing my cock , she gave it a few strokes and went right back to my ass. This was new to me she never touched my asshole like this before.
I was running my hands all over back of her nightgown enjoying the meeting of her nightgown with teddy. She moved from my nipples slowly working her way down to my cock. She took my cock into her mouth moving slowly up and down the shaft by this point I was going to exploded and screamed out "I'm going to cum" at this point she forced as much of my cock into her mouth as I exploded. I couldn'd belive she just let me cum in her mouth.
She came back up to kiss me, only to find out she still had much of my load in her mouth as she forced my mouth open and we shared my cum I could already feel my cock getting hard again. We slide our tounges back and forth sharing my seed untill we final both swallowed. I started to tell her how wonderful that had been when again I was told "shhhhhhhhhh we're not done enjoy" .
She sat up and slowly lifted her gown up just pass her knees and she said " baby tonight you are going to lose your virgianty" Thinking to myself what is she talking about she lifted her gown to show that she was wearing a strapon. I didnt know what to do I was in shock but yes I wanted that cock more then anything.
She turned herself around on top of me with the strap on inches from my mouth and told me take it suck it make it wet. I did as she wanted taking her cock into my mouth. Taking as much as I could and slowly releasing it then craming as much back into my mouth. Im sure she was enjoying me sucking her cock by the way she started to move with me, this went on for awhile then she lowered herself back to my cock but instead of sucking me while I sucked her she went right past my cock to my asshole. She licked my ass like I would lick her pussy around and around when all of the sudden I felt her tounge go into my ass I arched with the new found feeling. She didnt like that I arched my back and forced herself back down so that she could get back to tounging my ass. She forced her body down on me and her cock into my mouth so that I had to lay flat.
She had me pinned down spreading my legs further apart so that her could bury her head between my legs, flicking her tounge back into my ass. I was wiggling around with her cock in my mouth and her tounge in my ass. As I bucked around she slid a finger into my ass then two all while she licked away. She was probing my ass and I wanted to scream in pleasure but her cock prevented that.
She finaly slid her fingers out and rolled off of me and turned herself back around. She asked are you ready, I softly said yes. She lifted my legs and put her cock to my asshole, slowly but firmly started to push it against my ass. She pulled back and pushed forward each time putting more and more of her cock into me.
It hurt but the hurt was soon in the back of my mind as she finally got all of her cock into my ass. She stopped for a minute once she had her cock burried as far as it would go to let my ass adjust to it newly found freind.
She didn't wait long before she was slidding her cock in and out of me like she had done this her whole life. I was mummbling "fuck me yes baby fuck me" and boy did she. After what seemed like 20 min she really started to pound my ass, by this time i was screaming "YES BABY YES OH CORKY FUCK ME" when I felt her grip my cock and start jacking my cock to the rythem of her cock flowing in and out of my ass. It wasn't long and I shot another load all over my teddy at the same time she slammed her cock into me and held it as far up my ass as she could, I knew she was having an orgasm at the same time. She was quivering with her cock inside me and a death grip on my cock. We stayed that was for what seemed like 10 minutes her quivering inside me in some other world joined by her cock.
She finally laid down on top of me with her cock still in my ass, asked me "well did your day get better" all I could say is " I want all of my days to be this bad". She chuckled and said "babe this is just the start". From that day she was open to all my crossdressing and I was open to her newly found freind. I was Corkys girl now.