My Life in High Heels Ch. 02

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my continuing life as a cross dresser
1.8k words
4.56
40k
15

Part 2 of the 9 part series

Updated 06/08/2023
Created 06/03/2010
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cdandie
cdandie
122 Followers

Hello all, It's been some time since I last wrote as I've gotten very little feedback from my last writing. I love emails and comments and I don't bite unless asked to. The few letters I have gotten have all been positive and I thank you for the ones I've received..

I'm a cross dresser in the Pacific northwest. I have long hair which can be styled to suit my mood. I love wearing old fashioned lingerie which usually consists of stockings and a garter belt. I also go all out with various sizes of breast forms, makeup, outerwear and of course high heals. With effort I can and recently have passed in public.

From my last story you'll know I met two men Everett and Rex at an impromptu gang bang who have become regular lovers for me. We have also added a third man from that event. Ted, the gentleman with the amazing stamina had kept in touch and now has joined us. I required though, after that book store romp that all should be tested as I want to remain safe and clean.

Everett is tall, stout, brown hair, very strong, all male and possesses the largest cock I've ever seen on a man. It's long, about 10" I believe and an incredibly thick shaft with a head the size of a lemon.

Rex is of medium height, black, with a very thick cock as well. His body as well as his cock are jet black. When excited, which is most of the time, Rex's cock gets hard as steal and the veins are quite prominent on the shaft of his penis. I love seeing his cock when it's wet as it shines and glistens. It's also incredible to watch him pump in and out of me after he or someone else has filled me with sperm, as a frothy white lather forms and the color contrast is awesome.

Ted is lanky and lean, a runners build with a cock that bends upward, long thin shaft with a fat bulging lime sized head. All the guys are now shaved as I love the unimpeded view I get when bald.

All of the men are married but they all claim I do things their wives won't. I love lingerie, love anal and I always swallow. Go figure. Anyway, I meet with them individually about once a week and as a group about twice a month. They each bring me outfits they want to see me in and each one has his favorite idiosyncrasies which I try to satisfy.

Ted likes to lay over me with my legs hooked over his shoulders helping to support him. He uses his amazing stamina to plow my bottom for hours. Over the last year if you add up the time, I'm sure his penis has spent the better part of a week, firmly planted in me. Sometimes he simply pushes deep and flexes the muscles in his cock and I concentrate on squeezing or milking his cock as well. He'll put off ejaculating until he can't stand it any longer then moan and lunge deeply when he explodes. He'll quiver and tremble then fall onto me, completely exhausted as his cock finishes throbbing in me. Then he'll lay on me and sleep for an hour or better with his cock simply resting. When he begins to wake his penis will expand and stretch searching for more pleasure and we'll often repeat our lusty experience.

Rex likes to take me in numerous positions, usually testing my flexibility. He likes to slam into me hard and usually finishes with my rear hanging off the edge of the bed. His hands will hold my ankles or more likely my heels, spreading my legs as far as possible as he attempts to forcefully drive his cock up my throat from my bottom. Rex easily cums the most. Not so much an explosion as it is a river that flows. I'll leak for hours after he fills me and when I take him orally I must swallow several times to keep from choking. I'm sure it has something to do with it but he also has massive testicles which after a warm shower can hang six inches down and his scrotum is about as big as an orange but is jet black

Everett as I said has a massive cock and knows it. He already opens me and hits places in me nobody else has ever been able to but he still uses his cock like a weapon trying to spear me. His favorite position is with my stockinged feet on his thick chest. He hovers over me with my knees pressing my breasts together. My legs are pulled up with my exposed anal opening completely vulnerable to his relentless skewering. When he finally explodes he'll ram hard into me and rotate his pubic mound around causing his cock to propeller around my insides and his mound so mash my own testicles. After he finds his pleasure within my depths Everett like to use dildos and vibrators, sometimes several at a time to stretch my rings till my hole resembles a sloppy, sperm filled pussy.

When the guys take me as a group, they like to tag team me. One will fuck me till he gets close to ejaculating then he'll stop and let another take his place. I've been pounded like this for over an hour at a stretch. When they're finally ready to squirt they like to place several vibrating eggs in my bottom then put their cock in me. The vibrations and tightness causes them to drain themselves quickly one after the other.. I commonly will cum myself from the prostate stimulation.

They recently brought a harness that they hung from chains they bolted to a beam in the ceiling in my living room. They pick me up and lay me in the harness then pull my legs up and secure them in loops attached to the chains above my head. My bottom hangs over the edge, open and exposed to whatever abuse they have in mind. The upper part has a flap that can be folded back to allow my head to drop down and back letting them use my mouth for they're pleasure as well. Rex is the only one I can comfortably deep throat although it's difficult to swallow the volume of semen from him when my head is upside down. I've tried many times and I invariably end up with my nose and sinuses filled with his cream. It hard to imagine but I'm sure his sperm is swimming around my nose for a day or two.

When Ted tries to slide in my mouth in this position the fat head can lodge deep in my throat making breathing difficult. The guys like seeing his dick in my throat though. The head can be seen in my neck and they each take turns masturbating him by rubbing my neck. Besides fucking they're personal fuck toy in this vulnerable position they also enjoy sticking incredibly large objects in me. Multiple dildos fruit, vegetables and even they're fists will find a way in me. I have had past experience with fists and I'm finding I enjoy it more and more. When they spend the time they can make me have tremendous orgasms and can make me have one after the other.

My reason for writing this story is to tell of a recent event. After each emptying their seed in me the guys pushed a long wand type vibrator that was plugged into the wall into me. Then Everett, without giving my bottom time to adjust, slid his hand in me in a slow but non-stop push. I wanted to scream but Rex pushed his thick veiny black cock in my open mouth. He held my chin up not allowing any resistance on my part. The vibrations from the wand began and Everett held it against my prostate. I came in less than thirty seconds. I couldn't move as my arms and legs were bound. A cock and two hands held my head still and my anal rings were held motionless from inside. The wand continued it's attack on the sex gland in me. My post orgasmic relaxation didn't last as I came again in less than a minute. The assault on my prostate continued and I came till my convulsions didn't stop and I felt like bursting. The line between one orgasm and the next blurred. I have no idea how many I had. When the guys pulled themselves from me they all gazed at and played with my fat, sloppy, creamy pussy.

I had on a black garter belt with a pink panel on the front. It was covered with semen that had oozed from my own numerous orgasms. My hands and legs were unbound but weakness prevailed and I was unable to move. The men helped me up but I was trembling so badly they laid me back in the harness and let me recover. Ted and Everett ended up staying the night and helped me shower and got me to bed. They left my makeup on and dressed me in my DD cup breast forms with a suspender body stocking before putting me in bed so I knew they had plans for me later on . Of course I woke during the night to find Everett spooning me from behind with his ample spear probing my still sloppy bottom. Ted pulled my legs up and around him as he wormed his way between my legs I knew his fat headed monster would soon be seeking pleasure in my abused hole as well. It soon became very crowded as he squeezed himself in sharing my stretched ass pussy with Everetts throbbing cock. Not having the energy to move I simply moaned in my own familiar ecstasy and let these men pleasure their cocks within my creamy depths. Not sure how long it took but they both eventually bred me with fresh seed. They fell asleep immediately leaving their spent cocks wedged within my depths. We all woke in the morning with me in the middle with cum oozing form my bottom.

Everett got up and began cooking breakfast as Ted with his incredible stamina mounted me again. Looking down at me as he rhythmically pistoned in and out of my poor bottom he said that he wanted to thank me as he got more pleasure with me than he had with anyone else. He kissed my still painted lips and held me close as he thrust hard and trembled, breeding me with yet another load of fresh sperm. His words and act of intimacy was a cementing of my own femininity.

I do so hope you enjoy the description of a recent encounter. I have several others as well so if you enjoyed please respond so I know this brings others pleasure and is not a waste of time.

cdandie
cdandie
122 Followers
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6 Comments
TVFrannieTVFrannieabout 5 years ago
Please continue...

After reading chapter one I actually dreamed about your adventures last night and couldn't wait to read more today. I'm hooked! Your stories/encounters arouse and excite me! Thank you Lisa.

AnonymousAnonymousalmost 11 years ago
HOT!!

Your stories make me drip!!!

stusmithstusmithover 13 years ago
beautiful writing

Love your writing.... and the "plot" is great, too! Please keep going! I want to meet Rex.

heellovr69heellovr69over 13 years ago
Fucking HOT!!!

I'm so jealous, hon. I wish I had 2 hot studs breeding my tight CD cunt like these 2 are doing for you. I hope you continue writing more hot stories, they really get my clitty hard as a rock.

AnonymousAnonymousover 13 years ago

wish this would happen to me,,

im a cd also,,

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