tagTranssexuals & CrossdressersMy Life in High Heels

My Life in High Heels


Hello again all, I thought I'd write again about my life in heels and stockings. I work at home full time now with days being spent in front of the computer. I take frequent breaks working out on a treadmill and using a stationary bike. I rarely have to go out except to shop.

I also crossdress and when dressed I go by Lisa. I have brownish blonde hair and since I wrote last year my hair is now long enough that I no longer need to wear a wig plus I've added a few blonde highlights. Around the house or going out as a male I wear it in a pony tail but when I'm Lisa I will style my hair in various styles depending on my mood. Now since I can go for a week or more without going out I can also wear nails which besides walking in high heels was probably the hardest thing to get used to.

I have also kept myself completely shaved for years now, which once done, goes faster than you might think. A quick once over twice a week is all it takes. One word of advice, use the triple bladed razors. They do a great job and last longer.

As I said in my last story I have moved to the Pacific Northwest and meeting someone that enjoys my idiosyncrasy has been difficult. I have recently had some success but when I first moved here I had some frustration. Meets where no one showed up, meets where we couldn't click, etc. Sometimes a girl just has to do what a girl has to do. I had some eventful evenings with my toys but I'm writing to describe an evening I had at an adult bookstore which led to some lasting relationships.

I had checked out the store several times during the day and evening and on different days of the week to find out the best time to go as Lisa. There were theatres that could hold about ten people each in the back. Several showed straight films, one showed gay and one transsexual films. During the day older, retired men seemed most frequent and of course around five or so each day, men would begin streaming in and the place was packed for about two hours then empty the rest of the evening. There was a ten buck charge for all day except on Saturday when cross dressers got in free and couples were always half price. I decided to go on a Saturday afternoon when it wasn't real crowded and a few other cross dressers might be around because I actually was hoping to meet, compare notes and maybe play with another dresser like myself.

On the Friday before, I shaved extra smooth and ate a light meal with a glass of wine to help relax, and watched TV to keep my mind off the next day. Late morning on Saturday I cleaned myself out really good several times. Then I took a nice long hot shower. I had planned on wearing a loose fitting sweat suit and taking a duffle with my outfit and some other things. I debated with myself about makeup then just decided to go all out and go completely in character. Venturing out in daylight would be a first but I was exquisitely excited by this new aspect. I performed a magnificent job on the makeup and hair, looking very feminine and some-what slutty which was definitely my mood. I chose some simmering beige fashion stockings with a coffee colored welt that went high on my legs then pulled up some seamed fishnet stockings over these. I chose a black, ten inch wide contoured Lycra garter belt with eight straps that laces up in back. I attached four straps to each set of stockings for a very bound look. I perched myself on some 4 inch black stiletto pumps. My five inch heels look better but I can't drive with them and walking is quite difficult but I didn't purchase them for driving or walking.

I have several sizes of jelly filled breast inserts, a C-cup, a natural D-cup and some DD's that are made to stick out and provide me with a truly incredible cleavage. I can wear these with a clear Lucite cup less bra that harnesses them and holds them in place yet lets them hang naturally for a braless look. I also have several nice bras in several styles and colors that work well with them as well. I decided on the clear bra and the D-cups with a black opaque stocking top with sleeves over this. I wore a white sleeveless sweater over this and a black knee length skirt with a slit on the front side of each leg finished off my outfit. If I sat the slit would rise and show my stocking tops. Standing in front of the mirror I looked somewhat professional but the black seamed fishnet stockings exposed my true mood. I knew I looked more feminine than most women I ever come in contact with.

I grabbed a purse, put in it a little cash, a beach towel, some lube, a 7 inch dildo and I emptied a box of condoms into my purse as well and off I went leaving the house about 3pm. The drive over was uneventful, and there weren't many cars in the lot at the bookstore which I was happy to see as I didn't want to be overwhelmed. I walked across the parking lot, acutely aware of my heels clicking as I walked. In I went and instantly the eyes of the female clerk and three men who were shopping were watching me closely. I walked to the counter and told the clerk I wanted a ticket for the theatre's in back. She smiled and said OK.

Walking to the back my heels were LOUD and the men all began moving to the counter, I assume to buy tickets to the theater. I walked in the first room and found it empty with a woman giving a guy a blowjob on the film. I found no one either in the rooms showing gay or trans films. The next room had four men, all watching a cute blonde getting triple teamed with a group of blacks. I went to the last theatre and found nobody and on screen an older lady was taking some young buck doggie style. I sat for a minute to collect my thoughts and was soon joined by the four men from the other theatre. Watching for a while I got up and walked back to the room with the gang bang which it seems was a reflection of my mood for the evening. I took a seat on a bench against the wall to one side. Quite literally within seconds the four men who had followed me were back in here, as well as the three men from the front room who had been shopping when I walked in. Looking around, making eye contact, it was evident every guy was checking me out, waiting to see what I did.

I wasn't here to flirt or watch the movie so, my own clitty hard as heck, I stood up and pulled up and off my sweater. This allowed all to see my chest through the opaque material of my remaining top. I reached behind and unzipped my skirt then turned with my rear to the men I bent and slid my skirt down. I returned to my seat then crossed my stockinged legs. One of the men stood, walked over and never said a word as he fished his cock out of his pants. With some difficulty he managed to pry his erection out and a beautiful one it was. Thick, veiny and pointing skyward, I simply reached for the tip and slid my painted fingernails down the base. I wrapped my thumb and fingers around the shaft pulling it to my glossy lips. Looking up at my silent master, I engulfed his swollen member. I love the sensation of a thick cock entering my mouth. The spongy head and stiffness of the shaft are incredible to feel. I maintained eye contact with this man as he lost control. He put his hands on the back of my head and fucked my mouth, not allowing me any choice in the matter. He was excited from watching porn and so hard. I couldn't get his cock to angle down into my throat but it wasn't necessary as his cock erupted quickly filling my mouth. I continued to look up at him, maintaining suction and milking him with my lips and my fingers. As he softened I was able to get his cock into my throat allowing all of his sperm to flow straight into me.

Other men were gathering around me and I was helped to my feet and the bench was pulled away from the wall. With seven men surrounding me I was in a pure erotic zone. I could smell sperm from previous men relieving themselves and knew what was pointing my way. They helped me to lay down with my rear hanging off the bench. I reach for my purse and held out some condoms and told everyone that wanted to fuck was welcome but that condoms must be used. The guy that first lined up to use me had a medium sized cock that had a bend to the right. He rubbed lube on his sheathed cock then massaged my hole with his slickened penis. Other men held my legs and pulled them high till my knees were mashing my breasts. I opened my mouth allowing a man that was straddling my head from above me and dangling his cock in my face to feed his swollen member to me. As the throbbing cock slid over my tongue I felt the penis probing for my bottom find its mark. It slid into me whole in one continuous push, not stopping until the owner's pubic mound compressed my own testicles. My beach towel was folded up and put under my neck, thus bending my head back allowing deeper penetration of my throat. Luckily much practice has allowed me to overcome my gag reflex. Someone began massaging my neck. I realized they were jacking off the penis in my throat. I felt something hitting the bridge of my nose. Looking up, I was looking at the largest scrotum I'd ever seen on a man and it was straddling my nose and each ball was resting in my eyes. Luckily the owner was shaved and the lack of hair allowed me an unimpeded view of his massive swinging sperm makers.

As I concentrated on the fellatio I was performing on my lover, above me, the cock in my bottom rhythmically pushed my lips, mouth and throat in a steady motion, stimulating this cock to ejaculate. Within my mouth, were three massive explosions, filling my mouth with creamy cum. Those massive testicles above me were emptying themselves in my mouth. I tried swallowing as quickly as I could but at that angle and with this quantity, semen filled my sinuses and nose as well as my throat making breathing impossible. I felt the cock in my bottom thrust hard and the owner trembled. I knew it was spewing its seed, filling that condom, just a thin layer of latex separating my body from millions of sperm from an unknown owner.

Just when I thought I was going to pass out from a lack of oxygen, the cock in my mouth withdrew allowing me to breath. I looked up and saw the man in my bottom still trembling in final orgasmic bliss. He opened his eyes, smiled with his eyes and lips and mouthed a thank you to me. Another man straddled my head and pushed his very fat organ between my lips. When a man uses a penis pump their cock gets very swollen I've noticed. I felt the shrinking cock in my bottom retreat and another cock took its place. I reached down to stroke the shaft to assure myself that a condom was in place. Before I could reach it my hands were redirected to stroke other cocks.

I hadn't seen who was fucking me but he was quite long, hitting an area deep in me. I felt a mouth surround my clitty. I was in a blissful trance, just rocking back and forth, to and fro, as these cocks and a wet mouth stimulated my senses. I came quickly filling the mouth surrounding my cock-clit. The squeezing orgasmic contractions on the penis in my rear caused it to quicken till he was pistoning in and out of me at a relentlessly fast pace. The owner moaned and thrust uncommonly deep as his cock pulsed and spewed its juice. The man in my mouth held my chin up and snaked his cock head down my throat. I was unable to see as the man at my bottom pulled out so I never saw who this man was.

The men talked and I was lifted with the man in my throat standing yet keeping my head bent back and his penis firmly implanted in my throat. I was lowered and as I was lowered I felt a cock that felt like a phone pole, prying my hole open. I was lowered completely till this monster was impaling me. My legs were lifted high again and I felt another man working his way between my legs. The stiletto heels were like handles that allowed the men to control my legs completely. I knew what was coming but my legs and arms were being held and the cock in my throat held firm and the man under me held my hips down hard on his tree trunk like cock. This was the largest single cock I'd ever felt in my life. Excited, I was fearful of what was coming. I was feeling much too lustful to protest. Finally the second cock looking for my tiny hole found its way and forced its way past my anal rings. This dick fucked me with long stokes going almost all the way out then all the way in. The man under me began quivering. He wasn't moving much but being wedged tightly in the depths of my rear and the massaging from the cock he was sharing my anal ring with made him cum. He gripped me tightly and shoved slightly. Finally the dick in my mouth began flooding my throat. His cum was oozing more than squirting. He still held my head tightly, making certain that all of his semen was left in me. He kept his softening penis in my mouth. The penis on top in my bottom that was fucking me had amazing stamina. He fucked me relentlessly. Not slowing at all, he pounded my stretched anal rings for over twenty minutes. Finally the man under me who had relieved himself in me once already, tensed and came a second time. At that moment the owner of the cock that fucked me mercifully lunged forward and squeezed the back of my upward bent legs. He shook and jabbed his cock in short thrusts, as his cream poured from him.

The man in my mouth and the man on top of me retreated from me. I watched as another man who was black rolled on a condom. His cock was nice. Not exceptionally long but thick, thick the entire length of his cock and very stiff. He walked up between my legs and pushed his cock into my rear, sharing my tiny hole with the tree trunk cock from below that was still in me. I was able to look down and see this black tool slide in and out of me. This guy fucked me just as hard and just as steady as my previous lover. I saw and assisted my first two lovers jerk themselves as they helped hold my legs up. After some time they each squirted on my chest and face and the black man on top moaned and came in me as well.

After he finally pulled his limp cock from me the men helped me up. I looked at the man under me and his massive cock. Absolutely incredible! A gorgeous hunk of a man with a still hard cock that's size was the largest I had ever witnessed in person. I also noticed that the impossibly tiny condom he had worn was nothing but a ring with torn shreds of latex. I knew it was too late and it was evident from the sperm dripping from my abused rear that his several loads of sperm had bred me as well as possibly one other that I was unsure of.

I sat on the bench and rested. We all chatted while I rested then got dressed. Everett, who was the hunk who had barebacked me ended up being very congenial and he and I have become regular lovers along with Rex, the black man that I found I am also quiet compatible with. If the feedback is good I will write of some of our romps as they have been quite an experience. Thank you and I hope you enjoy.

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