My Life in High Heels Ch. 05

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Lisa's life continues.
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Part 5 of the 9 part series

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

Hi, Lisa again. I haven't written anything in some time. Not that I haven't had much happening. I just had to work through some events in order to know how they would turn out before I write about them.

As I stated in my last story the men I play with had offered to pay for a transformation procedure and drug expense to become a "woman". In my occupation I was capable of handling the expense but the offer from the men I knew was more of a request to make the transformation.

I had looked into the procedure but was unsure. There were stated possible side effects from the hormones and I personally I enjoyed sex, a lot and I did not want to have my desires inhibited. I spent a great deal of time talking with girls already on the program and I finally decided to go for it.

About three years ago I went to a Dr. and began building a relationship. It required some psychological testing and some health screening. Soon after I started the hormones which are a combination that produce the female attributes and suppress the effects of testosterone, the male hormone. I am quite slim and have an athletic build to start with but I noticed quickly that the little mid section fat I carried was dissipating and that after about three months it was settling in my chest and on my rump. Incredible to see it happen. I noticed when I laid on my side and looked in a mirror at my back side my "curves" were really developing. The guys did take notice as well and some of our encounters were exceptionally vigorous.

One of the men, Mike, from my weekend retreat at the sex camp had been persistent about contact. I have relented and he has become a part of out group. It has put more demands on my time but he has shared the expense of my transformation. Everett, who has become quite close and very much a confident said that he has gotten many requests for a return trip to the cabin but wanted to wait till I was further along with the transformation process.

My trips to the Dr. were an event in themselves. The assistants at the Dr's office were all encouraging and helpful as well as curious. They knew from my questionnaire I had had more than a few lovers and some of the women were amazed to find how much I genuinely loved having a cock take me anally. I needed to basically live full time as a woman. As my new hormones did their job I felt more and more feminine. My first trip to the Dr I wore sweats. By twelve months I went dressed up. I preferred nice conservative dresses, very feminine. Stockings, makeup, nice hair, confident, heels clicking as I walked. I love having my skirt or dress swishing around me as I walk. I've also found I really like the wrap around dresses. I can tie them at the waist and button a few button's and let the front act like a long slit when I walk yet it covers plenty when standing and when sitting I can cover or let the dress fall to the sides exposing my legs completely if I'm so inclined. I'm not afraid of drawing eyes to me as I know I am quite passable now.

The first procedures I had done were my face and neck. Mainly the nose. I wasn't bad with makeup, in fact with effort I could be hot but now I'm pretty good without makeup and very passable without any makeup what so ever.

Once my face was done I had my name changed so my documents could then be changed. I found these procedures to be much simpler than I imagined them to be.

Then last year I had a decision to make. Time for the breast implants. Of course the men all wanted monsters on the scary side. I on the other hand did want some size as I enjoyed approving stares but I didn't want to be a freak show turned into a carnival ride though. I am 5'11" and can carry some size, I decided on a D-cup or about 400 cc of fluid per breast to augment a little over 200 cc of natural breast tissue I had. I had to have tissue expander's inserted surgically to expand the amount of tissue to work with. This required an expansion to 600 cc per breast, 50 cc each week in each breast. This extra expansion is done to provide for a more natural breasts after the implant is placed and sewn in and a certain amount of scar tissue forms. I decided to go with the newer implants filled with tiny silicone pellets and thick viscous oil as I wanted a more natural breast without the rippling that occurs with the saline implants. These do however require a larger scar under the breast as they have to be inserted filled as they can't be filled once installed like the saline implants. You also want a surgeon that sits you up during surgury to check size and placement.

The day arrived and ended happily in a Demerol induced sleep. I will say this was not for the weak spirited and my hat is off to all the women that endure this procedure. It took about ten days to be comfortable with pain free movement but I will say I was visually inspired with my new enhancements. They looked HOT and the guys all agreed as well, evidenced by there teepee like jeans upon inspections. During surgury it was decided that 500 cc looked better on me so I came out of the hospitol a bit larger but happy non the less.

A word of caution though. My hormones were adjusted after this and my breasts grew another 150 cc of natural tissue per breast over the next six months giving me a total of about 875cc per breast which is quite a bit more than I was wishing for.

I decided to spend about a year now adjusting to living full time now before proceeding with the gender reassignment which I will have done in Thailand. I've been going to voice classes for two years to get my vocals up and I can now easily pass on the phone even. My confidence in public grows daily and it has been over a year since anyone was able to tell, even in everyday conversation. I love to wear skirts or dresses with a slit in the front. I have found they will get me out of every triffic ticket and a few date proposals

As for sex I still enjoy it greatly. My biggest worry was that I wouldn't crave sex the way I had but I guess it fills a need somewhere deep in me and I still think of it when its been awhile. I will say my plumbing is different though. If you're in love with your manhood this is NOT for you. The testicles will shrink some. I don't generally get into describing my penis size but it becomes relevant to something that we discovered that I will describe in the latter part of a gang bang that my lovers had for me later in this story. My penis, never large to start with, about 5" long and maybe a bit over an inch in diameter before when erect is now about 4" long and the shaft is about three quarters of an inch in diameter while the head has remained about the same size when erect but erections are difficult to achieve now. I still get excited but the reaction of my body is different now. I still have orgasms but they come from inside now and I emit very little fluid. When not erect my penis is about 2" long and about as big as a small finger.

The guys still enjoy playing (go figure) so we do so often. Sometimes singly, as a small group or recently all four guys and myself which was quite fun. This was the first time we had all played as a group since I had gotten my breasts. I wore a white boned corset that laced up the back. It had a rigid shelf cutout that supported and projected my breasts outward for maximum prominence. It tapered up to my neck to a collar around my neck, leaving my shoulders and arms bare. Three garter straps on each side held up some copper colored french heel seamed stockings with a dark seam and welt. I wore some 5" dark brown open toed stilettos with ankle straps.

My home is a renovated barn, nice with all the modern conveniences but with lots of wood and a heavy beam construction. The guys took one the downstairs rooms which I had used as a small library and from the overhead beams installs some hooks and they made a sling with all kinds off loops and attachments. They lay me in this sling and can attach loops and bindings in many ways, thus holding my body in place in whatever position they've chosen for me. On this occasion they had me simply on my back with my legs up and splayed wide. A ceiling mounted camera focused on my bottom hanging over the edge of the sling and showed the picture on a wall mounted flat screen TV. My legs forced up and out allowed my anal rings to open slightly in anticipation. The tip of a bottle of lube was inserted in my bottom and at least half the bottle was squeezed into me.

Mike was the first to enter me. He has joined us from my experience at the cabin and I have played with him one on one now a few times since. He is not a tall man but very athletic, very sinewy, he is very impulsive, and authoritative. He fucks me vigorously with one goal. ORGASM! His cock is nice, about seven inches but not very thick. This guy though can squirt some semen. Enough to put out fires. Not sure where he stores it all but I can drown in it if I'm not ready to swallow and he shoots it deep in me and definitely fills me up. He can and usually does cum twice with each encounter. Not much talking, only action. Afterward, a kiss and good bye as I lay in a puddle of cream.

Anyway, as he rabbit fucked my hole I expected him to thrust and fill me but after awhile someone yelled "time" and he pulled out and Ted entered me with his mushroom shaped cock with that puffed up head. He slid in and out with the camera focusing on closeups of my distended ring as his swollen lime sized head tried to partially pullout only to ram back in. Again "time " was called and this time Rex laid his ebony, steely hard pipe in me and again about two minutes in after time being called Everett moved up and put his monster at my opening. He slowing pushed, my body, sling and all. Being pushed up and away, gravity finally overwhelmed the tightness of my bottom and allowed Everett's tree trunk like cock to pop through my rings. Gasping from the sudden stretch, I felt Everett continue pushing, oh so slowly, but forging deeper, his shaft thickening with each passing inch. I had had Everett in me at least a hundred times and each time he entered me I felt like a virgin being opened for the first time. The depth and the stretch were always envelope pushing when this man probed my depth. As he hit the curve he had to move and adjust, snaking his way up my gut. Once he bottomed he rocked back and forth. The head of his cock plainly visible under my corset on my left side. Mike audibly gasped how incredible that was.

At the two minute mark the process began again with Mike taking his place this time spending one and a half minutes pleasuring himself in my bottom. The men each took their allotted turns, not cumming but building up. They didn't touch my breasts, allowing them to flop and flail, oscillate and bounce depending on the thrusts from my partner.

By the seventh go round the guys were only spending 30 seconds fucking me. Their cocks were as hard as I'd ever seen them, all pointing skyward and I could tell by the building level of excitement that large reservoirs of thick creamy semen overflowing with free swimming sperm would soon be unleashed and I was at some point very soon going to be the recipient of these pending explosions. Ted was the first to let go lunging hard and yelling. I could feel his cock throb. I've always loved, and today was no exception the feel of a cock pulsing in me, and today the pressure being released was exceptional. Rex entered me after Ted and fucked me for his allotted time. I always love seeing his glistening black cock turn frothy white as he fucks me when I'm full of semen. Today I was not disappointed as his cock dragged in and out, white globs of Ted cream. Evidence of sloppy seconds.

Rex was able to last to the next round and when his time was up Everett followed him in me. He took his time reaching bottom but once there I knew he wouldn't make it to the next round. The guys had left my breasts alone but at this point Everett squeezed my breasts and pinched my nipples. He pushed me and the sling about a foot with his penis, making a pyramid like structure in my stomach as it pointed skyward, erupting hard. Everett shuddered and trembled. I knew at that instant the river of semen that tends to flow from this man was painting my insides. As Everett withdrew, Mike entered me . Mike being much smaller and me being as cream filled as I was now, I barely felt him slide in me. All the visual stimulation had super stimulated Mike to the point that on the third thrust he shot off like a rocket A ring of white semen formed around his cock as he remained rooted in me. Mike bent down and sucked my breasts.

The guys had not spent much time playing with my breasts. I realized they were trying to last longer and didn't want the stimulation but when they were ready to cum they pinched, squeezed, sucked and slapped my boobs silly.

Rex still had yet to release his load and as he slid his black piston in me for what was now sloppy fourths, he looked into my eyes. We had been with each other enough and I could read the lust in his eyes. He was soooo ready to cum He was ejaculating before he even bottomed in me. His full pulses of cream breeding me again as my breasts were mauled in his palms. This was so HOT!

All four had tag team drilled me and now filled me. Rex and Everett took my feet out of the loops which had held my legs wide and helped me down. They had me bend at my knees and squat. Perched on my high heels with my gaping hole hovering inches over a mirror on the floor, ropes of gooey semen oozed and fell to the mirror. Strings of sticky cum spanned the distance and then a large glob appeared, then plopped out and fell to the mirror to a large "ooh" from my admirers.

Standing, the guys clapped as Mike handed me a glass of wine. The first toast was to my new breasts which all agreed were a raging success. I slipped on a white mid thigh opaque robe and we went and sat on the sofas, relaxed and recuperated.

This was only the beginning of this evening and it does get much much more interesting. Something was yet to occur that certainly had never happened to me before, that's for sure. If you enjoyed this story and want to hear more and certainly the rest of this evening, write some feedback and let me know so I'm not wasting my time. Thank you so much to the few that have written.

cdandie
cdandie
122 Followers
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6 Comments
TVFrannieTVFrannieabout 5 years ago
Livin' the life in heels

My God gurl (soon to be girl), when I first started reading your work I got so excited because often something you would write reminded me of bits of my life. It was like you knew me and were writing of my exploits. But now... WOW! You are doing shit that I couldn't have ever imagined just a few weeks ago. God bless you sister and keep it up! And getting new boobies now too! Lisa is my idol. Got to read chapter 6 now. Kisses!

AnonymousAnonymousabout 10 years ago
Awesome

Your stories are so hot. I love them.

AnonymousAnonymousabout 11 years ago

Wow, I' m jealous!

TV_TyraTV_Tyraabout 12 years ago
you go Girl

Dear Lisa,

I have only recently discovered your postings and become quite fond of it.

I can very much relate to your wonderfully lustful encounters and so enjoy the taste of sperm in my mouth and a big hard cock stretching and filling my boypussy.

Reading more of your exploits is something I really look forward to.

You've got yourself a new fan!

Love, Tyra

bethycrwfrdbethycrwfrdabout 12 years ago
i love how you describe the pleasures of being a woman

i have considered breast implants, but i am still trying to make up my mind how large. i think a c cup is attractive and respectable for a woman. but when i wear artificial d cup breasts, i like how much attention i get from men. i am beginning to feel that i might go to a double d cup size, to show how much i like men staring at me. also, i think i would enjoy the feel of monster breasts bobbing in front of me.

anyhow, your story describes many feelings that i share; including how much i crave the feeling of men squirting their cum inside me. please continue these stories.

bethy

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