My Life in High Heels Ch. 06

Hi to everyone reading this. Lisa again. Thought I'd continue with the sex night I had with my lovers from chapter 5. Just in case you haven't read my prior stories I started simply cross-dressing and certainly have progressed over the years. I have been undergoing hormone therapy for a few years now, have had my breasts enhanced, a D-cup, One thing I forgot to mention in Chapter 5, when I had my breasts done I, at the request of the guys, had my nipples pierced. I don't generally get into piercings other than my ear lobes I relented and had it done while under. I don't have nor am I attracted to tattoos though. I have tried to be feminine but remain classy.

I have had electrolysis and removed most all of my body hair not attached to my head. I found laser hair removal has too many "yeah, buts". In other words it works sometimes, maybe, for awhile and it usually, probably won't have a side effect. Electrolysis is time consuming, but is permanent and safe and a 100+ year history. I have long styled hair and am easily passable in any public situation now. I have yet to have gender reassignment but will have it at some point in the future in Thailand.

As for sex I still enjoy it greatly. I will say my plumbing is different since I've been on the hormones. My testicles have shrunk 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 part of the 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 now about three quarters of an inch in diameter while the head has remained about 1" 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 three and a half inches long and about as big as a small finger.

On to the gang bang. I was wearing a white boned corset that narrowed to the collar around my neck. It was cup-less with a shelf, allowing my breasts to be uncovered yet pushed upward and together. My legs were encased in some copper colored french heeled seamed stockings held up with three garter straps on each leg. I was perched on some five inch stiletto heel open toes that I believe the listed color is dark goldenrod or a brown shade that matched my stockings quite well.

We now sat on the sofas, sipping some wine and juice and munching on a few crackers and strawberries. Each of the guys took turns and went and took a shower We had finished a vigorous round of sex. I had taken each of the four men in a kind of tag team timed event, where the guys tried to last the longest. The result was I was soundly fucked in my sling and was thoroughly lubricated with their copious loads of semen. As I relaxed, leaning back into Rex's shoulder I had my legs crossed and resting across Mike, I had my bottom on a towel as I was slowly leaking semen. I smiled as I imagined all the sperm wiggling in me. I loved the image of that, as combined with my attire, it always made me feel thoroughly feminine.

Mike got up to shower and Everett took his place. Rex had his right hand cupping and kneading my right breast. Everett bent and kissed me softly. I reached with my left hand and fondled his shaft and balls. Ted came over and sat on the coffee table and caressed my legs. We all retreated to the bedroom knowing more passion was in store. I lay on my side facing Everett, my upper leg over his hip I tilted my head up and was presented with a penis attached to Rex. Greedily I began devouring it using my years of experience. Mike was fingering my sloppy wet anal ring, stretched and wet and sloppy like a well used pussy.

Everett was slowly rubbing his pole against my corset encased abdomen. He reached with his other hand and began playing with my tiny penis. These men in the five years I have known and played with them very rarely touch my penis so this was unusual in itself. I had a mouth full of penis though and about four fingers probing my bottom so I didn't complain. I felt Everett begin to rub the tip of his swollen cock against the tip of my fledgling appendage. His pre-cum allowed our penises to slide easily. Everett began encouraging the tip of my penis into the opening at the tip of his penis. This stimulation caused me to stiffen slightly allowing him to slide his cock up, entirely engulfing my penis within his much larger penis Everett and I moaned from this incredible stimulation. I stiffened to my maximum. As he stoked his cock, his hand would bump over the ridge that was the head of my cock about four inches or not quite half way down his shaft. Mike was standing over us now filming and said he'd never seen anything so cool.

Everett announced he was going to cum. My swollen head was lodged in him as semen pulses hit my penis. I immediately felt pressure build against the head of my cock. Having nowhere to go a dam broke and Everett's pulses pumped inside me. Now I am not studied in anatomy so I was not really sure where Everett's sperm and semen were going in me, but there was no doubt that sperm not only was swimming in my bottom but was now finding a new home inside me. My bladder I suspected. Possibly elsewhere.

Rex pulled his cock from my lips to watch. Very gingerly Everett pulled away. Once we were uncoupled he pulled himself up and I used my tongue and lips to clean and retrieve any remnant of semen left in his penis shaft. Rex lifted my right leg and slid in, and began rubbing his erection against my tiny stiffy. I knew where this was going. The guys found a new carnival ride. I wasn't complaining as I had come very close to having my own orgasm when Everett was filling me. The opening in the head of Rex's penis is smaller so he struggled. Everett was now filming and I was now sucking on Mike. Rex persevered though and my tiny cock slowly impaled his black cock. Later on the video we could see my head sliding up inside on the underside of his shaft. Rex trembled and moaned the entire length. He said it was somewhat painful but also one of the most pleasurable experiences he ever had..

It was very tight so we moved very little. When I watched the recording of this later, Everett got a beautiful shot of the tip of Rex's penis mashed against my bald pelvis, his black cock completely enveloping my tiny penis. There was no visible sign of my penis. Rex ever so lightly stoked his shaft with my legs under and over him. Ted had continued pushing on my bottom with his fingers and now had all five in me up to the widest part of the knuckles. My senses were so alive. I was noisily slurping and swallowing all of Mike's cock I could get in my mouth and jacking off the rest of him in my mouth. I was on fire. I wanted sperm so badly. I felt my rings swallow Teds fist up to his wrist. At that point he began waving his fingers, fluttering my insides. I heard Rex bellow and felt that now familiar pressure build up. I gripped and vacuumed the jets of cream from Mike as he exploded down my throat. Mike as I believe I've said before squirts like no man I've seen before. I began having pelvic contractions that Ted later said actually hurt his arm.

I do believe I passed out from this orgasm. The idea of having semen flow up my penis was certainly hot and I'm sure added to the head rush as I don't really recall untangling or having body parts pulled from me but in watching the video I was able to watch as the fist was retrieved from my gaping bottom and Mike pulled from my mouth. Being unaware of my surroundings I didn't swallow and semen flowed from my lips and Rex had to wait awhile for my own erection to subside so he could comfortably slide his sheath off of my penis.

The guys disrobed me and helped me to the bathroom where Everett and Ted ran a tub of water and literally washed me. Now I could end here and let this go till another time but the just two weekends later we had a get together that was erotic and certainly powerful and so I'll go ahead with the details. By the way if you do enjoy hearing my story, please do let me know. Either by feedback or email. It's nice to know someone is enjoying it.

Anyway, I was informed after my soak in the tub that two weeks later I was to be ready for SEX, I was to be their whore for the night, I thought OK, what had I just been. I was more concerned about sleep at that moment so me and my pillow got acquainted. I put it out of my mind for awhile and concentrated on work as money doesn't grow on trees. The following week I started pondering my attire. I generally like to dress in kind of a retro classy feminine look but Ted had told me I was to be a WHORE. So slutty may be more apropos. I called and talked to Rex and Ted in an attempt to try and find out where we were going so I knew what to wear. No help, their lips were sealed.

I decided on an old standby. Slutty underneath, classy outerwear. Under I chose a cup-less black corset that went low, almost like an open bottom girdle. It completely hid my tiny penis. It had four straps on each leg to hold up my stockings. I needed dark stockings but black is so plain so I decided on some coffee colored stocking with a dark seam and a european heel. For shoes walking may be required so no more than four inch. Rain and maybe snow was forecast so open toes were out. I went with some four inch open side ankle strap black pumps.

For outer wear I chose a dark brown wrap around mid thigh dress. This dress wrapped around my neck and I had got it before I got my breasts. Since my breasts were larger than I had originally planned, this dress was somewhat tight on top, when buttoned on top it harnessed my girls so to speak.

When the evening arrived I was ready when the guys arrived. cleaned up, in and out so to speak. Hair, done up, makeup more whorish than I'm used to but as ordered. Everett told me to unbutton my top. Thinking we were going out I was surprised but I did as ordered. Once my dress was loosened Mike and Ted each took a side of my dress and pulled it apart and literally wrestled my nipples out in the open. Everett opened a small jewelry box and took out a small ring. He opened a clasp and forced the ring into the piercing in my nipple. He repeated this on my other nipple. Then he took out two thin gold chains and attached them to each nipple. He then pulled them together very tight and locked them together. My breast were now being squeezed together by having my nipples stabbed and bound. My dress was then returned and buttoned up. My nipples and their bindings were plainly visible under the thin material.

Without comment they marched me out to a mini van and helped me into the back seat. I was blindfolded before we left the driveway. Driving for about an hour I lost track of my bearings so I was totally unsure of my surroundings but had been with these men long enough to trust them totally so I relaxed and simply enjoyed listening to the dynamics of conversation among friends.

We turned into a parking lot and slowed so I knew we had arrived. I assumed I would have my sight restored but instead was guided out of the van. I was on asphalt as my heels were clicking. It was raining now so my thin tight clingy dress was somewhat more clingy. I was guided up a step and through a doorway and the rain stopped. Some low mumbled conversation which I was unable to make out, before I was led further into the building. They say when you loose a sense your other senses become more potent. I'm not sure if that's the case but I have become somewhat of an expert on this odor. I smelled sperm. Very soon after I heard a woman in the throes of an sex. An adult theater.

We made a turn, walked a bit more, I was turned and my dress was then untied, unbuttoned and removed. Everett whispered in my ear this was the anniversary of the day we all met and asked me if I trusted him. More cold than out of fear I shivered but shook my head yes. I was lifted and placed in a sling and I felt my arms and legs being pulled and spread. Opening and exposing and restraining me

My blindfold was removed. Looking around there was my four men and about four others in a small theater with your typical adult video going on the screen on the wall. Rex announced that I was his whore. I needed to be trained and had to take all who wanted some but all must use condoms. Mike took a bottle of lube and squirt I believe the entire contents in me. The first cock entered. It was evident I was a whore. No name, just a hole for their pleasure. Not one entered me slowly, concerned whether it was comfortable for me. More men were coming in as the evening wore on. I had several offer their cocks to me to suck and, yes I may have wanted to but with condoms only. They all wanted to go bare. Don't blame them and I do love sperm but safety first.

I noticed several times that Ted and Rex were collecting the condoms from everyone after they shot off in me. I didn't think much of it After several hours 36 cocks now deflated, had filled 42 condoms full of semen. All the men hung around to watch the action. Rex put all these used condoms into three fresh condoms. He then tied a knot in the end of these condoms. He had Ted squirt some lube on these three semen filled balloons. He walked up to my open legs and put a tip of the condom against my loose anal ring and pushed and squeezed. The condom expanded into my bottom. Once part of it was inside me the fluid was sucked in pulling the entire balloon inside. This was repeated until all three of these condoms had disappeared in me.

Here I was strapped in a sling, surrounded by strange men now jacking off, who had just shot their cum in me in condoms, cum that was now floating in condom balloons in me. Mike appeared with a butt plug and began working it in me. I had taken larger plugs but not with sperm bombs floating in me. I had assumed that once released I could simply squat and expel these balloons but not with this plug. As the plug was being forced in me several guys walked up and began ejaculating on me. I told them "tits only" which they seemed to respect. Very quickly my breasts were slimy with a sheen of thin cream spotted with random clumps of semen much heavier in density.

Here I was with three pool ball sized balloons of ejaculate in my belly, a butt plug was being forced inside me, an army of cocks were relieving themselves on my breasts and after wards each one would usually slap his softening cock on my tender nipples or the chain binding them together and I was studying the varying consistency of their ejaculate. As the widest part of the plug was stretching me I was scared now. I shivered a few times and this wasn't the cold. I loved sperm, the sight, smell, taste, texture. Everything about it I found compelling and I had agreed to be a whore, sure and for the last few years I had been a personal whore for these men but I was scared now. These men had violated my trust. Particularly Everett who I had become quite close with and I was locked up on his eyes now as the plug seated itself.

I do not write a story until I know the outcome. I was released and I wasted no time getting dressed, I walked straight through the store and parking lot to the van. Once in the van I basically ripped that plug from my ass, squatted and expelled those balloons from my body. Now I will admit, once home I put several vibrating eggs and my inflatable dildo in me. As my orgasm racked my body the image was of all of the sperm from strange men swimming in portable fish bowls in my belly. Closest thing to rape I had ever experienced. A very dangerous event but one I wasn't going to waste without an orgasm of my own.

New ground rules are in place and my trip to Thailand is coming soon. Let me know if you enjoyed this. Not always but have been known to even answer email sometimes. Thank you , love you all, Lisa.