"Not MY Type?"

I’d known Kelly for most of my life. Growing up I spent most of my time at her mother’s house. It was a way to escape and avoid my parents constant arguing and fighting. It was a pretty well established fact that Kelly was lesbian early in Junior High School. Her mom and I became quite close as I was rapidly replacing the little girlie daughter she was losing to an ever increasing “butch-ness”.
By twelve years old I essentially become like a member of their f****y. Over the next few years they had the opportunity to watch me morph from a small frail Christopher into a pretty, petite and very feminine “Chrissie”.
After High School Kelly and I went away to college together and shared a dorm room for a year and then an apartment.
Being like a member of the f****y of course I was invited to her b*****r’s wedding. Kelly returned home several days before the wedding to assist her mom with the preparations. I had an important economics exam that week and was going to follow later.
Everything worked out fine and arrived a Kelly’s house the day before the wedding. It was very hectic getting ready for Scott’s nuptials but we still found plenty of time to relate old stories, tell some new ones and of course consume too much alcohol.
The evening prior to the ceremony all the guys in the wedding party took Scott out to give him a hearty send off out of bachelorhood. It was well after One AM and after copious amounts of drinking and smoking I was ready to call it a night. I clumsily made my way up the stairs and prepared to pass out in the guest bedroom. This was a room I’d spent many nights in while growing up.
In my slightly inebriated state I rummaged through my suitcase and managed to find my baby blue mid-thigh length nightgown. It was all satin except for an upper lacy section that covered my breasts. The straps were the thin spaghetti type. I struggled to divest myself of my clothing and laughed to myself at what a spectacle I must be making. After tugging my T Shirt up over my head and off I fumbled with the clasp of my push-up bra but finally to open the little hooks and the bra fell to the floor. I briefly cupped both breasts and gave them a little heft. It’s become kind of ritual for me when I dress or undress. I guess I’m subconsciously checking to make sure there still their. It took me a while to grow them and I never want to be without them again. I unzipped my jeans and with no small amount of difficulty managed to shimmy and tug until I got the tight fitting denim off my hips and headed down my thighs. It was a bit easier to get them past my knees and finally they lay in a pile around my ankles. I stepped out of them and bent down to retrieve my nightie.
I slipped the nightgown over my head and let it tumble down to my shoulders. I pulled it down further over my breasts and let fall past my waist. I kept my cream colored silk and lace trimmed hip hugger Victoria’s Secret panties on beneath the gown and prepared to collapse onto the bed.
Once in bed I lay their, closed my eyes, and wished the room would spinning. I don’t know when it did as I quickly dosed off.
I don’t know how long I’d been asl**p before I was startled awake by the presence of another body in the bed beside me.
There was no way I could tell who it was in the dark room and I whispered “Who’s there?”
“It’s me Chrissie and I’m too d***k to leave.” he laughed.
It was Kelly’s cousin Terry who had also come to town for the wedding.
I had known Terry almost as long as I’d known Kelly so I wasn’t at all frightened. Terry new the entire story of Christopher/Chrissie as most of Kelly’s extended f****y did.
I had by back to Terry and managed a little laugh as I said “Just don’t you try anything while I’m sl**ping.”
He bent down toward be and kissed my cheek. “Chrissie, I’ll admit you make one cute girl but you’re not my type.” he whispered.
Within a few seconds Terry was asl**p and I rolled further away from him and attempted to fall back asl**p. Thankfully I was it didn’t take very long.
Then sometime during the night or more like early morning I was awakened my the feel of a hand slowly caressing my fanny through the fabric of my nightgown. I started to jerk away but soon found an arm wrapped around my upper body. One hand was groping for my right breast.
“What the hell are you doing Terry?” I mumbling in s sl**py groggy voice.
Terry gave out a muffled laugh and said “ I got an amazing vision during the night and I decided that you might just be my type after all.”
Terry being nearly twice my size trying to get away was futile. As he groped my breast he wrapped a leg around my lower body which further immobilized me.
“Just what do you plan to do Terry?” I asked him.
“Well Chrissie, believe it or not I was hoping to fuck you.” he replied.
He held me tightly against him and I could now feel his stiff cock pressed against my ass. To be completely honest I did not find the feeling unpleasant and I asked him, “Aren’t you at least going to kiss me before you fuck me?”
He his head down and began to nuzzle my neck. I turned my head toward him in order that he might be able to reach my lips. He responded by kissing me on the mouth. Slowly and fleetingly at first and then deeper with more passion. He released his hold on me and removed the leg which was restraining me. I rolled onto to my side to face him and again we began to kiss. After several minutes of deep passionate kissing with our tongues entwined he reached to tug the spaghetti strap down off my left shoulder. He pulled far enough down to expose my left breast and immediately began to kiss and suck my hard little nipple. His tongue made little circles all around my nipple as he alternately sucked, kissed and nibbled on my breast.
While Terry was occupied with my tits I reached down slipped my hand into his boxer shorts. I wrapped my fingers around his cock and slowly began to stroke the stiff member.
He paused momentarily and smiled at me.
“Just making sure you’re up for the task as hand, Terry.” I said.
He lay back with his eyes closed and seems to be enjoying my soft hand as it manipulated his ever stiffening dick. I cupped his balls and stroked his dick for several minutes.
I paused and when he opened his eyes I smiled and said “Let me show you what else this girl can do,”
I reached for the waistband of his boxers and began to yank then down. He raised his hips up off the bed to facilitate my tugging.
Once the boxers were down around his knees I bent down and began to run my tongue around the tip of his penis. I wrapped my lips around the head of his cock and slowly began to take it into my mouth. I soon had my lips gliding up and down his shaft while I stroked it with my hand. He began to moan in low purring sound as I continued to suck his cock.
“Oh Chrissie, mmmmmmmmmmm…….What a good little cocksucker you are.” he whispered.
“Admit it Terry it’s the best you’ve ever had.” I smiled.
“Oh baby!!! Yes……….So fucking good!!” he said.
Once his cock was good and hard as well as nice and wet I rose up to my knees between his outstretched legs. I hiked my nightie up nearly to my waist and straddled his legs. Using my left hand I pulled on the elastic hem of the panty until I’d uncovered the entrance to my “pussy”. Using my right hand I guided his gorgeous cock toward the opening to my honey pot. I eased myself down upon his cock and felt it begin to slip deeper into my ass.
I began to move slowly up and down on his cock, seemingly taking it deeper with each downward motion. The pace of my bouncing increased and he began meet each bounce with thrust of his own. He f***ed his cock as deep up into me as he could manage while I rode him. I wanted to feel his cock even deeper inside me so I quickly dismounted him and assumed a position on all fours. He rose from his back and positioning himself behind me he swiftly rammed his cock into my “pussy” and began to pound me with ever more healthy thrusts.
“AAAAAAAAAAAAAAHHHHHHHHHHHHH……….like that……..just like that………..AHHHHHHHHHH!!!!” I said.
He continued to ram his cock deeper and harder inside me, stretching my poor tortured “pussy”. And I loved every minute of it.
He extracted his cock from my love hole and I slide down off my knees and lay there on my tummy.
He smacked my ass cheeks several times and asked “OK Chrissie. Ready for the grand finale?”
With one swift thrust he slammed his cock back into my well used cunt and began to plow my “pussy” with long, hard, deep, piston like thrusts.
“OHHHHHHHH YESSSSSSSSSS!!! BABY YES!!! OH FUCK YES!!” I said as he hammered away at “pussy”.
I was stroking my own barely 3” long “clitty” as he ravaged my ass. I was using a pillow to muffle my screams.
Finally his assault on my “pussy” stopped as I felt him pull his cock from my ass.
“AAAAAAAAAAAAAaaaaaaaaaaaaaaaaaaaaa!!!! “ I heard him utter as I felt his cum splash against my ass cheeks. Spurt after spurt landed on my little round bottom and dripped down betweens the twin mounds of my ass.
Terry lay down next to me and I just smiled and said “Not your type eh?”

100% (14/0)
Categories: AnalShemalesTaboo
Posted by chrissieCD
2 years ago    Views: 1,334
Comments (6)
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1 year ago
Morning wood is so special thanks Chrissie
2 years ago
2 years ago
Great Story Chrissie, thanx for sharing.
2 years ago
As much fun as that was to read, I just know it was a lot more fun to experience.
2 years ago
As usual this is HOT HOT HOT. And as usual got me hard as hell!
2 years ago
Great story! Love reading what you write.