My Life in High Heels Ch. 04

Hi all, Lisa here again. Haven't written in some time. I've been very busy with work and even "squeezing " in some play. If you've read my stories you know I'm a cross dresser in the Pacific northwest. I still work out of my home office and as a result of not having to go to work on a daily basis I can be in character for days or even weeks at a time. I'm becoming more comfortable and confident about going out as Lisa and am very good now at not being "made".

My hair is now down to the middle of my back and styling it is now easy for me. No more wigs for me. Makeup is still the most difficult part of this lifestyle but I've become much more capable and can adapt my look to suit my mood. The voice when out was always my weakness but by training one hour a day for months it's now second nature. For a lady my voice is still somewhat deep put it is decidedly feminine and quite passable now. I have also purchased an electrolysis machine which was an expensive decision.

As you've hopefully already read I have three men, Everett, Rex and Ted that I meet with regularly. I'll save time by not going into their descriptions so please read my prior story. The guys have spent many hours using the electrolysis machine on me. The time spent was extensive but the results have been extraordinary. I am bare. Underarms, chest, legs, what little was on my back and of course my groin. I was thinking about leaving a triangle of hair above my penis but the area got smaller and smaller till I was totally bald. This does save time on shaving but now I don't have to contend with stubble or that notorious culprit, razor burn.

This winter the guys informed me they wanted us all to be tested again. We had all been tested when we started playing together but I was impressed with this prudent behavior. Of course we all got clean bills of health and a week later the guys informed me they had a road trip planned for us all. They wouldn't tell me where we were going or what they had planned. I knew that ultimately I would be their play toy and suspected a secluded hotel was our ultimate destination. Not sure why but hotel rendezvous always make people hornier than usual.

I asked the guys what I should wear or pack and they said they would pick my wardrobe. This made me nervous as I suspected I would be traveling as Lisa and the unknown would have been easier to accept while not in drag as my travels in drag have been limited and controlled by me.

On Friday morning I dressed in my chosen attire. Coffee colored shear stockings, a dark brown 6 strap open bottomed girdle with a matching bra that held my spongy DD cup breasts inserts in small pouches. Luckily they let me wear some brown pumps with only three inch heels making walking easier. They chose a sky blue wrap around dress that tied at the waist. This was great to look at but when I sat the dress has a tendency to fall to the sides in front leaving my legs to and slightly past my stocking tops completely exposed. In looking at what they packed for me I had some interesting attire and I could see that much was in store for me.

At 8 am the men picked me up. Before allowing me in Ted handed me some bottled water. And told me drink it. I told him if he didn't want to stop a lot I probably shouldn't. He told me it was an order, not a request. Obediently I did as told. Ted drove his mini van and had the middle seat taken out. Everett rode shotgun while Rex and I had plenty of room to stretch out in the back seat. We drove for about two hours then pulled into a diner to eat. I was nervous as hell but trooper-ed on. There were several locals drinking coffee or having an early lunch and my attire certainly brought some stares. I sat on the inside in a booth and made an attempt to keep my legs covered when sliding in. The meal went surprisingly well and the waitress bought my look completely even referring to me as "honey". I used the ladies room and noticed that I was cramping some and really needed to go. After a good bit of time I felt relief and emerged washed then reapplied my lipstick before leaving.

Once on the road again I relaxed and even dosed a bit. Conversation ranged, sports, politics, women and the guys displayed a lot of curiosity about how I got started cross dressing. It wasn't long and I had to stop again to relieve my cramps. The ladies room at the roadside rest stop was very handy.

I was concerned a bit that I was sick and Ted informed me not to worry. This was the water I drank this morning just cleaning me out good. After awhile Rex asked me if I would consider something for them. He said the three of them would certainly pay for it and would assist me in my recovery but they wanted to know if I would consider getting breast implants. Honestly I had considered this and even pondered a total sex change. It wasn't so much that I was all that enamored with my penis or testicles but I truly loved sex the way I was. Looked forward to it at all time like most men. Granted, my peccadilloes are somewhat different than most men, but I am what I am and there's no point denying it. My fear was that if I lost my testicles my hormones would change and my lusty desires would diminish or change altogether.

Getting implants would be something I couldn't walk away from so I told the guys that I would consider it for awhile but it would take some serious contemplating. They agreed to leave it at that and about ten minuted later we turned into a nondescript entrance. No sign, only a simple mailbox out in the boon docks. We drove up to a massive and gorgeous cabin surrounded my tall conifer trees. We pulled in and parked in the parking area next to one other truck. Getting out we all stretched our legs and back. My guys, always the gentlemen carried my luggage as well as theirs. We entered the front door into a large great room. A young man came over and shook hands with the guys and introduced himself to me as Eric. I knew he'd had correspondence with Ted when he said to Ted that he was right, "she is absolutely gorgeous". Eric than said let me show you to your rooms. We went up a massive staircase then down a long hallway.

Everett and Rex got the first room on the right. I was given the first room on the left. Ted was given the second room on the right and Eric told him that they would be full this evening and as they discussed he would share with someone else. Ted let him know that was fine.

My room had a wonderful bed, tall beefy posts and rails with a thick comforter. Very masculine look. I large flat screen, two big comfortable chairs, and a beefy chest . The bathroom was spectacular. Very roomy with a warm water bidet. The tub had stirrups for the users legs and a hose with an assortment of attachments which were obviously meant for cleaning ones self out. I was getting the impression this was some sort of hedonist playground.

I lay in bed and tried to rest but the butterflies prevented a blissful nap. At 4:30 a knock at the door found Ted letting me know to come down for supper. I walked down the hall to the top of the stairs. Walking down the only sound in the grand room was the click of my heels.

Eric held out his arm which I took and he led me to the dining area to a table where my guys were already seated at. They rose in greeting and Rex pulled out a chair allowing me to sit. They were making it quite clear that I was the female here. I felt so provocative.

The meal was light Salad and main course. Very tasty, small portions topped off with a very nice home brewed wine which I'm sure had a higher alcohol content than normal. Everett finished his meal and excused himself early and went upstairs. Later when I finished my meal Rex said it was time for us to go up and get ready. He escorted me up and at my door he put hand on the back of my head and pulled me to him for a deep kiss. He then whispered in my ear with his deep raspy voice that I should clean myself out deeper than I'd ever cleaned.

When I got in my room Everett I assume had chosen an outfit for me, as one was laid out on the bed.. I commenced to cleaning myself out. The cramps during the day had done their job as I was virtually empty and clean but I still let the warm water from the hose and wand fill me deeply and followed with at least a dozen good flushes and finished just laying in the tub letting the water flow in and out of my bottom. I finished with a long soak in hot water with some scented oils. Upon getting out, my skin was smooth and so soft. I started with my hair then I applied my makeup, soft, virginal look that was in harmony with my chosen outfit.

I started with my smaller D cup breast forms that were laid out. These were smaller than the DD's that I had worn today but were spongy and flopped around more like a natural breast. Sitting on the bed was a tube of skin glue to attach my breasts to my skin. I've used these glues before but found they either don't hold or they hold to good and are painful to remove and usually require a day or two or three to weaken enough to allow easy removal. Reluctantly I applied the glue and attached my breasts. I then slipped on the white corset with six garter straps. This corset was shear from the top of my breast up then wrapped around my neck with a collar. It was cut to ride low in front and had an elastic tube sown on the inside of the front that held my penis up against my stomach in a glove like sleeve.

I heard men talking in the hall. Everett knocked and came in. He asked if I needed help. I said he could help tighten my laces in back. Everett was gentle yet forceful, pulling and cinching my girth into an impressive hourglass shape. My firmly attached knockers were jutting out now quite impressively.

Being so bound up dipping my toes into my stockings was a chore which required help from Everett. He helped get these beautiful pink colored stockings up my legs and making sure the black seam was straight. He also attached the side and back garters. Then he even slipped on my white stiletto's which had four and a half inch heels. The french heel on the stockings looked so exotic.

Everett left the room but quickly returned with two glasses of the house wine. As I stood in the mirror inspecting the finished look Everett came and toasted me on my look and said I was as hot as I'd ever been. I looked in his eyes and asked him if I would enjoy tonight. He hugged me and assured me I would enjoy this evening and to relax and trust him as he wouldn't let anything bad happen to me.

Next he pulled out of his pocket a white blindfold. Once I was sightless he guided me to the hallway which was silent. Once in the hall someone else held my left hand and guided me to the left down the hall away from the stairs. Being blind and in heels I was completely reliant on the strong hands guiding me for support and balance.

We entered a room, then I realized we were in an elevator as we began descending. We exited the lift and I realized we were on a tile floor which I had not seen yet today. I was led about two dozen steps, my heels, again sounding loud and provocative. I smelled something, a soothing lavender candle I suspected. The men on my sides gently turned me then each reached behind my knees and lifted me in a swoop. They then backed me and laid me on a thickly padded table that supported my back and head leaving my derriere hanging slightly. My legs were pulled open with my knees slightly bent and my ankles were bound tightly. The entire table was then tilted back further leaving my head tilted back slightly. A strap was pulled snug around my waist binding me to the table.

There was no conversation, when I suddenly felt a tongue licking the back of my legs and I could tell by his cologne that Rex was kissing my lips. The tongue on the back of my legs moved toward my pussy and kissed and slightly penetrated. A penis began to nudge my lips. Instinctively I parted my lips allowing the swollen gland access to my moist mouth, I could tell this was Ted by the shape and size of his penis. I suspected Everett was fluffing my bottom but was unsure as none of the guys had shown a desire to orally stimulate my anal rings. The tongue withdrew from my bottom. Rex kissed my ear and whispered to me "do you trust us"? I hesitated but said yes. He took my hand and guided it to another cock on one side which by it's size I knew was Everett's. Rex returned and asked me again if I truly trusted them. I shook my head yes while nursing on Ted cock..

I felt the pressure on my anal rings of what I knew was a penis. Ted's was in my mouth. Everett's was in my left hand and Rex was kissing my right ear. This was an unknown cock forcing itself into me. Rex whispered to me not to worry as everyone at this club was tested and that I was the center of attention for the weekend. I trembled but was brought back to reality when the new penis pushed forward in one motion and bottomed in my pussy. I knew this was only the beginning.

For the next hour numerous cocks pounded my bottom. No one came. As soon as they got close, the owner would pull out only to be replaced by another. Luckily someone squirted what felt like an entire bottle of lubricant in me Finally one man lunged and grunted and I knew from the voice it was not someone I knew and I also knew this man was relieving himself in my body. I was allowed use of my hands and arms and as the men pounded into me I wrapped my arms around each and every one, welcoming them and verbally encouraging them to exert themselves and find pleasure in me.

After everyone had ejaculated at least once in me and Everett lazily stroked my depths with his spent yet semi erect cock. Someone nudged my mouth. I opened and a cock slid in. I sucked and stroked and massaged the spongy head with my tongue. I could hear men jack off over me. Hands were squeezing and tugging my breasts. With these firmly attached I now knew exactly how a woman felt when hers are manhandled. Men were commenting on how hot I was and that Ted was right, She was really good. I took pride and worked even harder at bringing these men that surrounded me pleasure.

Soon I felt semen splash on the cock in my mouth and run down the shaft into my mouth. Someone said that was so hot. Another commented that they were glad this was on tape. Soon others began squirting on the dick using my mouth and in very short order as I held my mouth open every cock in the room drained itself in my mouth including the cock inhabiting it. Being slightly inverted and having a pulsing cock in my throat, made swallowing difficult and that familiar feeling of having my sinuses fill with semen over took me. I enjoy the thought of this, but the results of this last about ten days. I have drainage down the back of my throat and the odder of sperm overwhelms my senses and all food tastes like semen and sperm. A constant and lingering reminder of my escapade.

After all were empty my bounds were released and my blindfold was removed. Looking around the men all smiled and as my legs were trembling they lifted me up and all supported me once standing. Everyone hugged me and thanked me for allowing them to use me. There were four other men besides my three.

I was dripping copious amounts of sperm and lube from my pussy so I was given a towel then escorted to the elevator. Once in my room I sat on the towel on the side of the bed and Ted helped me out of my pumps. I made my way to the bidet and allowed the flow of water to massage and clean my pussy. Making my way to bed I collapsed and slept the entire night rolled up in the comforter still wearing my outfit.

The next morning I awoke and laid for some time in bed pondering the night before. I realized I had not cum yet I still felt amazingly satisfied. Rex knocked and came in. He asked if I was hungry. I said yes and asked if they were still picking my wardrobe. He said I could wear something comfortable but he certainly liked what I had on. He offered to help me get my heels back on and helped me teeter down the stairs into the dining hall.

The men from the evening before were eating breakfast and getting ready to leave. As each one finished they came by and hugged me expressed their gratitude. Once finished with breakfast I strolled into the great hall expecting the guys to tell me to get ready to leave but they were lounging by the fire and informed me that I could rest for the day here and we would leave the next day.

I went up and changed into some shorts and a tube top. The breasts were NOT coming off so the large nipples and dark aureolas of my breasts were plainly visible through the thin material of the spandex tube top.

I read a magazine and lounged and chatted with the guys and with Eric who was the caretaker. It seems this place was used as a hunting cabin in the fall and for groups to rent the rest of the year. The group that rented it that night had been a group of men that gang bang women. Usually wives while the husband watches or participates. He said I must of made an impression as they said that was the most fun they had ever had and I gave better blow jobs than anyone they'd ever had here.

He asked me if I had always been gay. I explained to him that I had started out simply cross dressing not explicitly thinking I was gay. I had had women and certainly appreciated everything about a woman to the point of even trying to act like one and that somewhere along the way I picked up an appreciation of men as well. It wasn't so much hetero vs. gay as much as an overwhelming desire for all things sexual.

He asked if I wanted to be a women. I told him he was not the first person to ask or to offer to help me become one. I also told him that would require more thought on my part. I asked him what he thought about it. He said I was certainly better at being a women than most of the women he had seen here. Eric asked me then what it was like sucking a cock. I said you either enjoy it or you don't. There are women that enjoy it and women that don't. I do I said.

He then asked if taking a cock in my ass hurt. I said when I first began trying with dildos it was painful on the initial entry but the pleasure far outweighed the discomfort. Now though I had no discomfort at all. He asked if I was now stretched out. I explained that I seemed to have as much control as ever but have learned how to relax and allow myself to open. Eric then asked if it felt good. I explained that if I was stimulated inside I could have an orgasm without touching my penis, but that I got most of my pleasure from having my partner experience pleasure. I told him I had not had an orgasm the night before but felt totally satisfied. Much like a woman can enjoy sex without an orgasm. "Men are goal oriented and set out to achieve an orgasm as soon as they begin having sex, that's the male makeup, instinctive propagation of the species type of stuff". Ted spoke up and told Eric if he was interested he should proposition me. Eric looked at me with a "can we" look in his eye. I nodded yes and whispered to him to meet me in my room when ever he felt comfortable.

Eric asked me if I slept around a lot. I said I always did what I could to make sure people I'm with are clean and that though rare if I get the "can't help its" condoms are an option. He asked if I would have sex with anybody, I said I used to have prejudices, fat people, old people, etc,. but that age had mellowed me and that maturity has allowed me find something good in everyone I meet. A smile, nice hair, nice voice, great personality. Never met a soul I couldn't find something to like about and worth loving.

As we continued chatting I began to feel my cramps again. I looked at Ted and asked if he gave me that "stuff" again. He smiled and said I'd been a good girl to drink all my orange juice that morning. I had to excuse myself and go relieve myself. This was not to bad though as I was generally clean from the day before, hoping not to gross readers out but mostly just loose watery clumps of cum. While sitting in private I realized that if Ted had given this to me again I was going to be performing again tonight. I decided I needed a nap. I cleaned my face of all makeup and slipped into bed.