My Life in High Heels Ch. 09

For those of you reading my stories they are not in chronological order. Not any order for that matter. Just writing as I reminisce of my past. Also I appreciate all the wonderful responses. Thank you. If you enjoy reading them I appreciate the atta girl.

This is how I got my serious start with groups of men. I had cross-dressed for many years. A wonderful lady helped me in the beginning and after we moved from each other I was alone in my thoughts and feelings for a long while. I would dress and built a large collection of clothing. I also longed for touch, a human connection. I wished to be taken like a woman. Like most cross-dressers that experiment, I inevitably practiced being taken by a man, I used various objects and really enjoyed anal stimulation and practicing my oral skills..

In my quest to bring realism to my experimentation I began shopping in various adult stores around the city I lived in. I built a collection of phallic objects, small, large, smooth, lifelike, soft and flexible, hard and rigid, vibrating, battery, plug in industrial strength, I had a probe for whatever mood I was in.

As my wardrobe and skill in dressing improved I experimented going out. First in the dark of late night, just driving around at first, Then stopping at gas stations, then shopping in stores. As my comfort level increased and my ability to pass improve I started going out during the day. I worked on my voice and was able to pass quite easily. I eventually began shopping for my adult toys dressed. Some of the stores I felt very comfortable in, others not so much.

I eventually met a guy, then another and built some relationships that progressed to the point of being sexual in nature; however that is not what this story is about. Eventually I got to the point where I was comfortable with what I was and basically lived as a female. One evening when I was at one of the stores I knew well, one of the cashiers who I had talked with often, asked if I was interested in a safe swing club. I had never contemplated this. He explained that there was a group of men, all gay or bi men that got together once a month at a home on an area lake and had sex. He said they all professionals, classy and clean and really enjoyed the company of a well dressed cross dresser. It lasted for a Friday night through Sunday morning and everyone could stay as long as they wished and leave when they chose.

I asked again to make sure if cross-dressers were welcome as I liked to dress as a woman. He said a few have attended and they seemed to enjoy themselves and return periodically. The ones that had were well taken care of he said. with a wink. He said I could wear whatever I chose and could stay dressed as long as I chose. He did warn me that if I dressed as I did in his store that I would be very popular. I tend not dress slutty, more classy, sexy business like. I don't care for cheap lingerie that falls apart quickly. I wear only six or eight strap garter-belts that hold up my stockings well to avoid wrinkling. I also used good realistic breast forms with a lot of bounce that stay in place and nice lacy bra's or corsets. The stockings I use are full fashion from the best manufacturers.

Telling him I would think about it I left. Once at home I couldn't sleep that night. I was so excited and scared at the prospect. The next evening I went in and told him I would try it. He smiled and said great. He gave me a card and told me I had to go to this clinic and get checked. I was impressed at this hurdle. I asked a few more questions to alleviate my fears. He said it was to late for the current month but I could easily make it for the next month. He also told me best behavior was required or you would be asked to leave and not be allowed back. He also said another cross-dresser was supposedly going to be there the next month. This was appealing to not be the only dresser there.

I went to the clinic and met with a nice Dr. who was on the card. He drew blood and had me lay on a table with my legs in stirrups at which point he took several swabs. I did not go dressed but he made me feel so comfortable I wished I had. Afterwards he said someone would call me in a few days. A few days later, sure enough a gentleman called me and said he was with the club and gave me a date, time and address. I was not familiar with the area but told him I would find it. He said if I wanted, a car would be available to pick me up. I was nervous about this aspect as I wanted a way home if need be. He said to think about it and he would call the week before to see if I wanted a ride.

Time went so slow for the next several weeks and my nerves were jumpy. I got my call on Wednesday before and I accepted the ride. He said there would be several people I would be riding with.

On Friday afternoon I began my prep, A deep thorough cleaning. I shaved my body again being careful to get every stray hair. Another good cleaning and a bath followed with a light aromatic body oil. My hair, long enough not to need a wig now, I fixed it wavy, fluffy and airy and light on spray to keep it in place. I began to dress. It's been many years since and I still remember exactly what I wore. I started by making sure my breast forms were securely attached and aligned. Good and tight for the weekend. I chose a two tone purple and lavender, boned open bottom corset with six wide strong garters. I slipped into some lavender fitted full fashion stockings with a black welt and black foot and seam. I finished with an almost sheer, grayish blue dress. I chose some gray four inch heels with no ankle straps. Very easy to take off. I packed a bag with some makeup and two changes of other outfits and a really hot one piece swimsuit I had modified myself.

I was ready and sitting on my couch, nervous, A knock made me jump. Opening the door a pleasant looking 50ish gentleman smiled and asked if I was Lisa. I said yes and he smiled picked up my suitcase and waved his hand to a waiting limo and said after you. I walked to the waiting car and the door from inside was opened for me. I slid into the back seat and was greeted by a young passable woman my age who introduced herself as Robin. Another gentleman, about 35 sat across from us. We made our introductions to each other and small talk which I can't remember. I remember sitting with my legs crossed and the man across from me relentlessly staring at my stocking encased legs.

After about an hour of driving out to the lake country we pulled up to a gate which opened and we drove up a secluded drive to a majestic home with beautiful landscape and low light illumination. We all walked in through the massive front entry and I saw about twenty five well dressed men in age from 30 to 60. Most with a drink in their hand and talking in groups. Looking around Robin and I where the only ones dressed as ladies and there was no women present. I was introduced to the group and most all tilted their heads and the closest ones shook my hand and welcomed me. Robin told me in the car over she had been here once before with eight other men for one evening and had had a wonderful time. This group was much larger than I had anticipated but everyone seemed very courteous and gracious. I was asked what I drink and I had a glass of wine.

After a very short time I saw a few men begin to neck and a state of undress was soon seen throughout the room. I saw Robin busy with three men, Two men began to lead me to another room and to a stairway to a basement. It opened to a large open room with TV's along one wall and many couches and in the center hanging from some chains from large beams in the ceiling a swing. I was led to a couch near the swing by one gentleman and once I was standing near the swing the other man came up behind me and took my empty glass then reached for the soft satin buttons on my dress top. He kissed me deeply and my dress fell to the ground. He had me sit on the couch and placed his hands on the sides of my face and told me how hot I was. I knew what he wanted and I leaned forward and slowly and timidly took his manhood into my mouth. I was good than at performing oral on a man and had practiced often with dildos so I knew how but I did not have the skills then that I do now. I think a man is best suited to know how a man likes a blowjob performed. I found myself concentrating on making sure I didn't rub my teeth on his shaft. It's such a second nature now it makes me laugh.

I continued sucking and slurping with my eyes closed. I don't know how much time passed but I soon felt his hands on the back of my head. I felt him tense but not having the experience I have now I was oblivious to the signs and I still remember being surprised by the burst of semen in my throat. At that time I had not yet developed a taste or desire, yearning if you will for a mans cum. Now I crave it. In all parts of my body. At the time I had had it before but the need for it was not there yet. That would soon change.

I dutifully allowed him to empty himself in me and did not pull away, instead holding him in my mouth and allowing him to pull out. I opened my eyes and was greeted my three nude men. They helped me to my feet and one swept me up and placed me on the swing. My head was slightly elevated but not much. I was almost flat as my legs were each pulled up and placed in a loop and a small silk tie was wrapped around my ankles, holding them in place. My strapless heels hanging on my toes. My first suitor lined up his already lubed cock and slid himself in and another cock was offered to my lips which I greedily accepted. My free hand was pulled and wrapped around another hard cock. I soon felt the man in my bottom lunge slightly and knew instinctively this man I didn't know was giving me his seed. There were very few words, a few moans while ejaculating, some directions to me to suck in a certain manner but mainly just constant motion with intent to put as much cream in me as quickly as possible. After the man in my bottom pulled from me the man in my mouth took his place and the man in my hand pulled my head to line up my mouth with his throbbing cock. Looking up I saw the sweet Dr. who had tested me at the clinic. My free hand was pulled to stroke yet another erection. I lost count of the number of cocks I serviced, maybe ten but all finished in my now loose and very sloppy "pussy". My initiation if you will.

When finally none was left with an erection I looked around the room. Most were sitting on the couches enjoying the show and I finally noticed I was in full view from several angles on the TV's that lined the wall. This aspect scared me but I was still randy as heck as I had yet to come myself. I was already finding myself to be submissive and I gained my pleasure from others pleasing themselves with me but I still yearned for a release.

I was helped up and looking around realized I had been on the swing for about two hours. One of the gentlemen asked me if would like to stay overnight in a room or if I required a drive home. I agreed to stay and he said a room would be prepared. Many of the men came up and kissed me and thanked me and said I was a welcome treat. Soon I was led, still only dressed in lingerie with a squishy sloppy creamy bottom by a nice man through the house and other men to an upstairs room where my clothes and bag already were. I was given a glass of cranberry juice an oat bar and two pills from the Dr. He explained they would help me clean out easily in the morning. I drank, ate and swallowed my pills. I slept like a baby. The next morning I had a light breakfast and was given two more pills by the Dr. I cleaned out very easily on a table with stirrups with Robin and several other men.

Everyone was wearing swimsuits around the pool so I changed into my high neck black one piece. It held my breast-forms tightly together and gave me quite the profile. I had altered the one piece so that there was about a 6" opening on the backside. I wore shorts so as not to show my suits surprise until needed. The water felt great as I swam a few laps. A man I had not been with the evening before swam up next to me. We chatted for awhile and he reached his arms around me, pulled me tight, I lost my grip on the side and unable to touch the bottom I had to hold onto him, Another man came up behind me and my shorts were slid down. Fingers began to search and my available bottom was a welcome surprise to the men making me into a sandwich. They pulled me to shallower water and continued the sandwich, all the while caressing my body. One reached for a bottle of lube on the edge. The skinny nipple of the bottle was pushed into me and a healthy squirt was pushed into me. My legs were pulled up and around my lover in front of me and he let me settle on his stick. I easily slid down on him. The man behind me nudged up close and ever so slowly pushed himself into me as well. I just put my face into my lovers shoulder and moaned as the two cocks in me found a rhythm.. They stood still and bounced me on their erections. I was not used to this kind of girth in me at that time and I was in pain and exquisite ecstasy. Very soon the man behind me held my breast forms tightly and moaned as he lunged and filled me with juice. In quick succession my other lover filled me as well.

I was slowly released from my puppet masters and led to the steps and then to a large lounge chair. I was laid down and almost immediately mounted. A quick succession of men with stiff penises mounted me and fucked the hell of me. As I recall, five men found relief in my depths while in the lounger. I moaned and yelped when ever one bottomed really hard and a few cat calls from the watching audience cheering on whoever was fucking me at the moment, words of encouragement telling the man on top to "fuck her hard" or "tear it up", other than that there were few words. I was, after awhile helped up with my sloppy cunt awash in man cream. I went and sat on the edge of the pool. A puddle of cum formed as it seeped from my full pussy. I looked over and Robin was led over wearing pink stockings, a pink garter-belt and bra and was laid on the same lounger I was just on. Men lined up and fucked her relentlessly. Watching her I saw her with her legs held high, where I just had been and she was now getting what I had just got. I saw men tense up and knew their stiff cocks were filling her up just as I had been moments ago and another quickly took it's place. When they were done I saw her pussy, gaped open with a large dollop of white semen at the opening. This was me earlier and I was so hot at the sight.

After lunch I was asked if I was ok with staying and said I would try and stay. and told not much happened on Saturday afternoon so I went upstairs to my room to relax. Robin was in the hallway and she invited me to her room for "girl" talk.

Robin told me this was her third time here and that they seem to like to have two or three passable dressers to act as whore's or simply a cum dump. She said the man at the adult store was the conduit for everyone here and that everyone here must be checked at the clinic before being allowed here. She said that if I'm accepted I will be routinely checked and will be told not to NEVER have sex with anyone outside of this group when I get in the car to leave. She said during the month some of the men will arrange to get together with her for sex. I asked Robin why they simply don't get women to do what we do. She said she thinks the men here are all gay or bi and like the fact that we, as submissive male cross-dressers are more willing and accepting to take much more than a woman.

Robin and I became good friends to this day even though we now live far apart. We spent many nights satisfying a group of men.

After our talk I went back to my room and rested for awhile. around four in the afternoon Robin knocked on my door and asked if I was wanted to start getting ready for the evening. She led me downstairs to the room set up for clean-outs. I took my place on the padded table with my legs in the stirrups and my bottom hanging out over a trough. A young gentleman assisted with this task. Warm silky water flowed into me. On my back and watching in the mirror, I was amazed at the amount of spent cum still in me. I was filled and sucked empty over and over till I was sparkling clean. A fairly large dollop of coconut butter was pushed into me.for a finishing touch. When Robin and I were done we walked back upstairs and talked over our wardrobe choices for the evening.

My first night I had worn business attire, sexy but classy. This evening I would be a bit more slutty. I chose a black eight strap 11" wide garter belt, a black long line lace bra and a collar with a steel loop and matching wrist collars. I slid into some coffee colored, seemed stockings and stepped into some black five inch heels with a hearty strap around the ankle, with a steel loop in the straps as well. I pulled up a tight and oh so short shiny leather skirt which did nothing to hide my stocking tops. I fluffed my hair up and was heavy on the makeup and red lipstick. I did my nails in bright red as well. I was ready for anything and wanted all involved to know it.

Robin soon knocked on my door and we walked down the stairs together. Once in the main hall I noticed a few different men were present and a few of the previous men were no longer there. Robin and I and a new "lady" were the only women present. After a short meet and greet everyone went downstairs to where I had been the evening before and I now heard was referred to as the playroom.

I knew it wouldn't last long but as soon as I got downstairs one of the men came and kissed me deeply and someone behind me slid down the zipper holding my skirt tight. Once loose it was yanked down and I was left in my lingerie. I glanced over to Robin and the other "lady" and they were both surrounded and quite occupied like I was. I was quickly blindfolded and led by each hand for about twenty steps. Difficult in five inch heels. My hands were pulled up and I felt something attached to the loops on my wrists and they were pulled high and tight. My leg were lifted and a strap of some sort was wrapped around my legs on my knees and it was tied high and very wide. I was now suspended from my wrists and knees with my legs spread as far open as I could spread them.

Without any foreplay I felt what I knew was a hard man was attempting to gain entry from behind me. He was well lubed and slid in with a slight lunge and a pop. I was evidently not to high off the ground and he pushed up into easily with good leverage. He very quickly erupted. Immediately after sliding out another took his place. as he slowly worked in me. I felt another mans body pressing into me from the front and getting himself in position between my spread legs. His cock sought entry into my already occupied cunt and with a lunge my ring relented and gave way to his forceful thrust. These two men fucked me in unison. Both going in and both coming almost completely out at the same time. They maintained this rhythm til they neared orgasm and then just pushed hard in to me. I was stretched tight enough to feel first one then the other cum by the throbs of the pulses of ejaculate.

I was very quickly filled with two more cocks. These men were taller as the pressure on my wrists dropped and I was basically a puppet, propped on two pulsing hard sticks. These two men were also sticking me with meat, much larger than I had been given all weekend. They more less bounced me up only to have me fall back down on these two massive logs trying to rip me open. One of the men I could feel has a bent cock and was hitting me in a place deep inside that was mildly painful. I said so and he lunged harder, taking pleasure in my discomfort and inability to stop it. My submissiveness took hold and I just said "please, give it to me harder sir" They both pounded me hard about thirty more seconds and then filled me again.