My First Time Dressed for Someone

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My first time dressed for someone and eager to please.
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I walked out of the bathroom into the bedroom towelling myself dry as I went. I felt very strange, an odd combination of apprehension mixed with a low level of sexual excitement. My stomach was quivering slightly and I had a vague feeling of weakness. I could hardly believe that tonight, if things went as planned, I would come out of the closet for the first time and, hopefully, learn to make love as a woman. This night was to be the culmination of almost twenty years of gradually accepting the fact that I was gay as well as being a transvestite. Countless times in the past my nerve failed as I stood before the apartment door. My fingers, beautiful with bright red false nails and lovely expensive rings, cold with fear, would simply refuse to turn the doorknob. Tonight, I hoped, would be different. Thanks to the ads I began corresponding with others about my sexual and transvestite desires.

Gradually my fears subsided and I resolved that I would attempt to meet someone who seemed compatible. After some false starts I finally began to correspond with David. He sounded exactly what I was looking for. He was not a TV but was my age, said he enjoyed French and Greek as the active partner and occasionally liked to experiment with bondage and photography. In his photo he seemed very nice. A pleasant looking, smiling, open face about 6 feet tall, rather on the husky side but not fat. Masculine but not hard looking. I quivered with sexual anticipation every time I looked at his photo. He lived in the Washington area about 2 ½ hours drive away. In his last letter he included his phone number and asked me to give him a call.

I did and we hit it off immediately. He had a delightful soft, deep voice and had a marvellous, understanding sense of humour. I explained that I was still a virgin, so to speak, but was wiling to do anything I could to satisfy him. His reaction was that was even better and he promised to be gentle and understanding. I knew that I would have to meet him face to face. It was a Tuesday night that I called and we arranged for him to drive up on the following Friday night with the idea of staying the weekend.

Wednesday and Thursday nights were spent cleaning the apartment until it was spotless and shopping for groceries for the weekend. On Friday afternoon, I took my pink satin sheets and pillow covers out of the box in the closet and placed the fitted bottom sheet on my queen sized bed. Then made up the rest of the bed. The top quilt was a gorgeous frilly satin pink also. The bed now looked sexy and feminine, ready for the orgy I hoped would follow. I stored away all the items on the dresser that could be construed as masculine. By then everything was ready except me.

It was then about five o'clock and David said he expected to arrive around eight. I went into the bathroom and stripped, examining myself in the full length mirror. I decided that I was altogether too hairy. It had been some time since I had given my body a through shave. I filed the tub, added lavender bath salts and along with my Gillette seated myself in the steaming scented water. I started with my arms right down to the fingers. When my hands and arms were hairless I changed blades and carefully did my underarms and the few stray hairs on my chest. By this time from the waist up, except for my head, I was silky smooth. I changed blades again and started on my legs and feet.

I carefully whisked off the fuzz on the toes of both feet and started working up to the knee, first the left and then the right. I changed blades for the third time and started on my thighs, first the left, front, inside, back side ever so carefully. I didn't want any nicks or scratches to mar what were my most attractive feature. I repeated the same procedure with the right thigh. By then the water had a lot of hair floating on the top so I closed the shower curtain, pulled the drain, stood up and turned on the shower. I marvelled at how smooth I felt. Except for my genital area and head I was as smooth and silky as the day I was born.

As I stood in the forceful spray of the shower I had another brainstorm. Why not shave my penis, balls and asshole? I had never done anymore than trim it in the past. I'd always been afraid it would itch too much as it grew back. I pondered on the idea for a few seconds and then decided to do it. After all tonight was very special. I turned off the shower and retrieved my electric shaver out of the medicine cabinet. It has a sideburn trimmer on it and I thought I would try that to get the heavy hair off to the point that I could use the Gillette. It worked beautifully. Soon all that was left were very short hairs all around my penis, and virgin asshole.

I then lathered the area with shaving cream and carefully used the razor. I managed beautifully in front on and around my penis and balls but had a problem with my back side. Standing up was awkward and I couldn't see what I was doing. The last thing I needed was to cut myself there. Then I remembered the large round mirror in the dresser. It was the type that magnified on one side and was ordinary on the other. I set it near the drain of the tub. I lathered the area again and by lifting my legs up and manoeuvring the mirror get a perfect view of my ass area. With the water running just slightly to clean the razor I finished the job. I stood up and turned on the shower again to clean off the soap and lose hairs on myself and in the tub. Masses of black pubic hair clotted the drain.

After cleaning it all up I again showered using an expensive scented soap. As I stepped out of the tub and looked into the mirror on the wall, I couldn't believe my eyes. I was as smooth as a new born baby, I powdered myself with the same scent as my soap and decided to go into my room and get dressed for this very special erotic night.

I knew that this was to be a very special night for me and I decided to wear my most sexiest outfit I could muster out of my closet. I selected my short black satin pleated mini-skirt, that I had just purchased the other day, along with my new white satin blouse with the diaphanous sleeves and the low cut front. I took out my new black satin bra and panty set and laid them on the bed. I then got out a matching garter-belt and black seamed silk stockings, laying them next to the other items that I had selected for the night. I went to my closet and took out my black patent six inch spiked heels that had the ankle strap, that held the glistening magical feeling shoes securely to my feet, all was now ready. I slipped into the bra and put in the false breasts that bounced in the bra as I walked. I slipped that garter-belt around my waist and fastened it with the hooks, then sat down on the chair and rolled my stockings up my legs, making sure the seams were straight. I stood up and stepped into the black satin panties and pulled my black satin mini-slip over my head to rest just below my garter belt. I place my arms in the sheer white satin blouse and buttoned it up the front, then I stepped into my short little satin mini-skirt and buttoned the side. I stepped into my six inch spike high heels of shiny leather and tied the ankle strap. I slipped on my earrings, rings, bracelet, neck and ankle chains.

I checked myself in the mirror. I was just fantastic, I looked very sexy and felt just as good, the only thing is that with such a short skirt I knew that when I sat down he would be able to glimpse at my stocking tops. Now to put on my make-up and I would then be ready for my very special night. The foundation went on just right and the eye shadow and mascara was just perfect, a little blusher to my cheeks gave life to my already excited face and the final items I used were long false nails and a glossy bright red lipstick that matched my nails to give my lips the sexiest look I could. I took my shoulder length light brown wig from it's box and expertly placed and styled it on my head. I was now ready. I stood up and took one final look at this desirable looking female staring back at me from the mirror, and said to myself, "Baby this is the night you have been waiting for."

I left the bedroom to finish with dinner. The table was set for a romantic dinner. My best China, a candle and a bottle of wine chilling, the steaks were in the broiler and were just about ready when the knock came on the door. It was David and he was just the perfect gentleman when he greeted me at the door and all through dinner, and afterwards as we sat at the table sipping the red wine and enjoying each other's company, getting to know each other a little better.

After dinner, David moved to the couch and I brought him a brandy. He said to sit down beside him and relax. I did as I was asked and he just looked at me for awhile, then he reached over and took my head between his hands, pulled me to him and kissed me. Lightly at first and then with increasing passion he invaded my mouth with his tongue. He pulled away and said, "Darling, I want your mouth on my cock right now, I'm ready to burst."

I said, "I want to desperately but I am just too afraid, force me please, tie me so I can't stop you, please, please David force me." He pondered for a moment and then said all right. He stood up and walked into the bedroom. He came out in a moment carrying his case and a satin pillow from the bed. He placed the pillow on the end of the coffee table and told me to remove my skirt and blouse and to kneel, in just my underwear at the end of the table and lie with my stomach and chest on the pillow. I did what he said and he opened his case and brought out a reel of very soft rope.

He opened a pen knife and cut off four strips of rope. "Put your arms behind you," he said. I did and he quickly tied my left wrist to my right elbow and vice versa. He then tied two additional strips around my arms, they were very snug and I knew that it was too late now to stop him as I would never get those cords off by myself. He then cut off more strips of rope and proceeded to tie my left leg, just behind the knee, to the left leg of the table and then another strip further up on my thigh. He repeated the same action with my right leg. My upper legs were now tightly secured to the coffee table legs. He then reached in the case and pulled out four wide leather belted cuffs with metal rings on them, he attached a pair of these to both my arms, just above the elbows, and a similar pair to my ankles. He then cut off a longer strip of rope.

First he knotted one end of the rope to the metal ring attached to the back of my left ankle. He then threaded the cord through the ring of the cuff attached to my left elbow then straight over to the ring of the right cuff and then down to the ring of the right ankle. He then began to pull on the cord which had the effect of raising my left foot off the floor straining against my left arm. When my lower leg and foot were about 45 degrees to the floor he reached down and pulled up my right leg to the same height and knotted the cord to the cuff so it would not slip.

My back side was completely exposed and the soles of my shoes were looking up at the ceiling. My head was sagging down as the pillow only went as far as my chest. He then took another belt with six small rings on it and wrapped it around my head at the forehead. When it was snug he took another thin belt with rings and wrapped it around my neck snug, but not too tight, just above the Adam's apple. He then tied different cords between the band around my forehead and the band around my neck, the object being to keep the forehead bond from slipping off. Then he took a longer piece of rope and attached it to the already once used left wrist cuff and ran it up to the left unused ring of the headband, over to the right unused headband ring then down to the right arm cuff ring. He stood behind me and gently lifted my head off the table and at the same time pulled the slack out of the last cord. When my head was raised enough to get my chin about three inches off the table he secured the rope to the right arm cuff.

So there I was fastened to the coffee table almost completely immobile. My head pulled back as far as it safely could be, my arms tied together and my feet sticking up in the air. Only my knees touched the floor and they were snugly tied to the table legs. David stood up and said, "There, you make a pretty picture if I ever saw one."

With that he pulled an expensive 35 mm camera from the case. He attached a small electric flash unit to the camera and walked around to face me. "David, please don't." I said, but I knew it was hopeless to protest. He took about twenty pictures from various angles and then changed the roll. After he changed the roll and attached a battery charger to the flash unit, he walked over to me and said, "Well, darling it's about time you had your first taste of cock." With that he began to strip. In a few seconds he was nude, he stood before me with a semi-hard-on. He had a lovely body just slightly fat but flat stomached and obviously in good shape, he was covered with soft brown/black body hair. Thanks goodness I thought, his cock does not seem to be too big. I was afraid it would turn out to be an 8 or 9 inch monster. I guessed it to be an average six inches uncircumcised cock. He sat at the end of the table, legs over either side facing me, his cock about a foot away from my chin. My mouth was gaping open because it was too much strain on the muscles to keep it closed.

"You want it don't you?" He asked, without waiting for an answer he slid up the table till the tip just touched my red lips. I couldn't pull away more than half an inch. I recoiled for a moment but couldn't stand the strain on my neck muscles and moved forward again slightly, with that he moved forward again about another inch so that the tip was just past my teeth. Neither of us moved for quite awhile. All I could hear was my breathing mixed with his breathing. I thought this is what I've waited so long to do. I began to fleck my tongue over the head and into the peehole. He moaned softly and moved forward a little more. He moved again and soon I had at least half of it in my mouth. I began to frantically tongue it's underside and press my lips to it as hard as I could. He moved and moved forward again this time much harder and suddenly the tip entered my throat. I suppressed the desire to gag with all my might. He didn't move and I just kept swallowing over and over trying to suppress the urge to throw up. Evidently he could feel my throat muscles working at the tip of his cock.

"Ah! this is heavenly," he said. With that he moved again forcing it in as far as it could go, my head was pressed back as far as it would go, my lower lip was forced hard against the soft sac of his balls and my upper lip against the hair of his lower belly. The tip of his cock felt like it was being enveloped by my tonsils. I continued to wretch and swallow continuously. I thought to myself this is it, I am going to die with a cock shoved down my throat. He suddenly pulled out halfway, paused while I caught my breath. Perspiration was running down my face and head. "OK, darling, this is it," he said. With that he plunged forward again as far as he could go in one thrust. Once again the tip slid into my throat, funny though this time it wasn't so bad. Once the tip was past the throat opening, the area behind it was smaller and I began to adjust to it. He didn't move, he reached down and held my head in his hands, I still hat to swallow continuously but the retching began to fade away. He just moaned and said, "You're just wonderful." My moans mixed with his and only my throat muscles were moving. He said move your tongue, I began to move it as fast as I could back and forth, from side to side, he moaned louder and said, "Oh God! Here it comes, take it all, swallow it," not that I had much choice.

He untied me and I went to the bathroom. I applied fresh lipstick to my mouth and went back out to the living room. As I entered he stood up and motioned for me to sit on the sofa next to him. When I sat down he put his arm around me and leaned forward and kissed me hard and long, then whispered in my ear what a lovely weekend we were having together. You can bet we did and we only left the bedroom to eat and bathe.

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AnonymousAnonymousover 5 years ago
BREAKING HUR IN

I've fucked a lot of trannies in my time, and find them to generally be a better screw than women. I do a lot of hill walking and often use the moors buses to get to/from a good area. That day a Dog Walker got on the stop after me and all the signs were there that he was a Faggot, who probably dressed. Within a week I knew where he lived and engineered a meeting in the local pub, which led to me taking him back to his place, and persuading him to dress for me. Soon he was in all white lingerie, Bra, Susspender (Garter) belt, stockings with seams and a tiny G-String which barely covered him. "Is the White meaningful" I asked, and he confessed to being a Virgin in all respects of sex with a man. In that session I started him off with my cock in his mouth, working up to a slow, if deep, throat fucking and Creampie Sundae to drink. My next visit I began to work on HUR (I always like to feminise them early, and named her A-MAN-DA) Pussy with fingers, KY jelly and various Dildoes, leaving hur overnight with a Butt Plug in her as I slept next to her. By three o'clock in the morning I pulled out the plug and Broke Hur In properly. I shagged her for about seven years before she had the full operation, and I wished her good luck and finished our relationship.

MarieJoanneMarieJoanneabout 7 years ago
Thrilling

This mirrors my own fantasy whereby I am tied and "forced" by a man thereby removing any say that I might have in the matter. Very very exciting. Marie

FemmeCharleeneFemmeCharleeneabout 7 years ago
Loved it!

Very nice dahling!

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