Playtime With A Sissy - Part 1: How I First Started free porn video

Playtime with a Sissy - Part 1 How I first started By Lisa Jade I enjoy dressing men up in sissy clothes. I suppose "enjoy" is not really the right word to use, as for me the experience is very much an absorbing sexual adventure, to which I have now become totally addicted. I know that I get just as much excitement and stimulus from our sessions as my poor sissy does. In fact I usually end up being wetter and in a bigger mess than he is. So let me take you back to when I first started, when I first stumbled onto the culture of sissies and dressing up. I became involved with this wonderful world of cross-dressing by accident. It was not a planned thing, but something I discovered about 5 years ago. I was on the rebound after my partner left me, due to my lack of commitment. She wanted our relationship to be a more open and proactive one. She wanted us as a couple, to be more involved with the outside world and was keen to meet my parents and my large extended family. I was horrified as I had spent most of my life hiding who I was and pretending that I was "little miss normal". (Don't get me wrong, I have grown up since then and now realize how stupid I was.) Yes, I made excuses and went about hiding our wonderful relationship to the extent that it forced a wedge between us. Then, after a frustrating few months, my girlfriend finally gave me an ultimatum, that unless I could be openly proud of who we were, our relationship was just too destructive for her to carry on with. Amid tears and heartache, my love left to head overseas, leaving our mixed-up affair behind her. My parents are strict Catholics, so I could only imagine the reaction if they ever found out that their only daughter was a lesbian! This burden of possible loss is, even now, enough to cripple me emotionally. I still need my family and that is the price I have to pay. My only saving grace is that they are country folk and I live a good 3 hour drive away from them, in the city. So, I was single again and hurting, scared and unsure. It took me a few months of isolation before I was really ready to face the world again. Sure, I knew that I was not ready to openly admit to my sexual bent, but I still went looking for those casual one night stands. Of course, most nights I ended up alone, with only myself available to self -serve my needs. It was through the clubs and bars that I started to get out and get my secret life back into shape. "The Pink Pussy Cat Bar" was famous for its special "girls only" events on a Thursday night and I soon became a regular there. The girls there are great, friendly, sexy and wonderfully supportive to lost souls like me. After one hectic Thursday night party at the club, I arrived back at my flat still single and extremely drunk. Thank god, I was not working until the weekend and that my next shift at the hospital was on Sunday morning. Friday was a write-off, but Saturday was spent cleaning the flat and trying to put some order back into my life. It was on the Saturday that I realized that I had lost my black lace shawl. I knew that I was wearing it at the club, so it after pulling out the wardrobe, it clicked that I must have left it there after my last wild visit. A quick phone call, confirmed that it had been found and so Phil the barman, rescued it from the pile of lost property, putting it in the managers office. My Sunday morning shift was surprising pleasant and I actually left work in an amazing good mood. As the "Pink Pussy Cat" was only a 10 minute detour from the hospital, I swung past the place to retrieve my shawl. Expecting to find a deserted venue, I was surprised that there was a gathering of ladies in the private function room, leading off from the main lounge. A low noise cloud came from that area, with strains of Blondie lifting up over the conversation hum. I was intrigued with this party, as it appeared to be a "girl" only event. Thinking that it was a possible special gay event, I became curious and decided it would be worth gate-crashing the gathering. As I approached the bar, Phil the barman caught my eye, nodding for me to come over to join him. He was serving a brunette, who from behind was just appallingly dressed. She was wearing a horrible white, black spotted, drop waist dress, with a black cardigan. It was so daggy and out dated; that I am sure the fashion police would have locked it and her away years ago. I know I was being rude, but I could not help but stare at this person and what she was wearing... Now, let me explain. I suppose I could be classed as ultra feminine. I do love fashion, clothes and exploring my womanly attributes, much to the horror of my bank account. One of my former partners would say that I am like this because I am trying to over-compensate for my taste in companions, who knows!! But I do drive all my friends crazy, with the amount of time and money that I spend on my clothes, makeup and hair. I just love dressing up. (Something I now know is what I share in common with cross-dressers!!!) "What can I get you, Lisa," Phil asked cheerfully. "Hi Phil," I smiled. "If you get me my shawl, I'll order a drink...Please?" "Sure thing." He nodded and disappeared to the back. Curious, I moved up to the other person sitting at the bar and drinking a beer. I wanted to see who in their right mind would wear such an outfit, for this person needed serious help. "Hi, I'm Lisa." The brunette turn to greet me and I was shocked to see it was a man in a dress. He had done his best with the make up, but still had not successfully covered the 5 o'clock shadow. The only saving grace was the wig, which was styled in a short luscious brown "bob". He blushed and his eyes took on that look of dread. "My name is Janine," the guy answered, trying to hide his maleness, by squeaking out in a voice that was at least 3 octaves higher that his natural tone. The poor man was scared out of his wits at meeting someone outside the group, and I could see he was bravely trying to weather out this encounter. "So what is going on here?" I asked, masking my initial surprise. Working in a city emergency department, has made me adept at hiding emotion, so I was able to continue as if this meeting was a natural everyday occurrence for me. Phil returned and saved the day. He handed me my shawl, which was a bit worse for wear for being screwed up in a ball and kicked around the dance floor. "So what about that drink," Phil asked slyly. Without thinking I asked for a glass of sparkling wine and turned to the "shrinking violet" by my side. "Left my shawl here," I said, holding it up and examining it for damage. There were not any holes or tears, just a bundle of creases and a floor's worth of dust. "It lovely," Janine said, fingering the lacy edge. "So what your story?" I asked, keen to know what was going on. Phil placed my glass down on a coaster in front of me. "On the house, Darling." He said flirtingly. "Why thank you, dearest." I flirted back. Phil was well aware of my sexual tastes and so knew that it was safe to banter without causing offence. "Janine was just going to explain what was going on here." Janine cleared his throat, and started to talk in that high pitched travesty of a voice. I reached out and gently grabbed his arm. "Be natural," I said. "Don't try so hard. Just use your normal voice." "Sorry," he stuttered. "I'm so nervous. The last woman who caught me dressed, kicked me out of the house and is now filing for devoice." "Once a month," Phil interrupted, helping the situation. "The local cross dressing club meets here, on the Sunday afternoon. They've been using this venue for about 2 years now." "So Janine, is this your first time out in public?" "Yes, no," he said flustered. And so I pulled up a stool and sat down for an interesting chat. It turned out that this was the 2nd time out for James / Janine. His wife had left him about a year ago, after catching him fully dressed. That and other things had caused the separation, and now he lived by himself in his own flat. As he opened up, I found myself being genuinely interested in what he was saying. I found myself wanting to know more about his lifestyle, where he got his 'girlie' things from and how he learnt about trying to be a woman. I had to refrain from asking that burning question of why, knowing that the same could easily be asked of me. Something did click with us, for we were soon laughing as he explained the problems he encountered while trying to buy a dress. After a couple of drinks, Janine introduced me to the other 'ladies' in the group. Again I was amazed at the lengths that these men went to, to be able to pass as a woman. There were certainly some who were even less convincing than dear Janine, but most were fantastic examples of the latest fashion and makeup. As I tired not to examine everyone too closely, I knew that even I could learn a trick or two from these guys. I must admit I was feeling dizzy with excitement. (No, I was not drunk, as I had only had 2 drinks!) Then, as I left, Janine gave me his phone number and asked if we could possibly met again, maybe for drink. For the next few days my mind was a buzz. I had found it exciting to be around a group of cross-dressers, men who wanted to be and act like women. The more I thought about it, in my perverse way, the more I found myself getting turned on, until one night I was heavily masturbating to the mental image of dressing a man up in a frock. I awoke the next morning hot and sweaty, with my new fantasy still fresh in my mind. Just laying in bed, and thinking of what my next move should be, in regards to this new stimulus, was enough to get me moist again. To a certain extent I was annoyed with myself, as I felt I was loosing control to a man, but as I started fingering my clitoris, I just knew that I just had to explore this new path that I had found. After I enjoyed a long hot shower, I gave 'Janine" a call on his mobile. He was at work and to my amusement, found it difficult to speak freely. I cut straight to the point and carefully explained that I wanted to help him with his cross-dressing. He was definitely shocked and started to mumble. Not fazed with his reaction, I told him that I would be over to his place on Sunday afternoon, after I had finished work. I know that I was smiling like a Cheshire cat as I carefully wrote down his address and hung up the phone. The weekend approached fast and I started to get nervous. It was only after talking to a few of the regular girls at the 'Club' on the Thursday night, that I was able to decide what I would be doing with Janine. Even though the general consensus was that I was just inviting a truckload of trouble into my life, a few of the girls were very familiar with the cross-dressing scene and so were able to give me some good ideas. As soon as work finished on the Friday, I dropped into the local charity store. There I bought a lovely bridesmaids dress, the only one in a size 16. It was made up of meters of the shiniest dusty pink taffeta, which tied up at the back with a large bow. I then took it across the road to the drycleaner, who assured me that it would be ready Saturday afternoon. Sunday morning presented me with another dilemma, what to wear. I must have tried on at least 4 different outfits, starting with a simple mid calf silk skirt and peasant blouse. One look in the mirror confirmed to me that it was a bit ordinary for what I was going to do. My LBD, (little black dress), looked good but showed no imagination, while the mini skirt, boots and Bolero jacket was a bit too casual . Finally I settled for my royal blue evening gown, with the single sash strap coming off the right shoulder. I do like the way the tight bodice pushes up my small boobs to create a cleavage. The slightly flared skirt, mid calf in length that floated down from my chest, gave the frock an air of elegance. The makeup, then took a good half hour, with most of the time being spent on trying to get my eyes looking just right. Then the hair, and another twenty minutes flew past. It seemed at the time that I would never get out of my place. Of course I tried playing around with a classic French knot and even with a simple bun. In the end, I decided to just wear my hair out. (Then I was a natural brunette, with shoulder length hair. Now after a few styles and colour changes, I am a blonde with a short 'bob'.) When I eventually left my unit and started the car, I knew that I was dressed inappropriately for a Sunday afternoon, but I not for what I had in mind. I had packed my makeup case, Janine's new clothes and I also threw in my old Wilkinson Sword electric clippers. I will admit that this it is my favourite toy. With the safety cover on, and the blade removed, it is a fantastic vibrator. As soon as I place the metal plate just on my clitoris, that first buzz, jolts me instantaneously into wetness. (So, while I am being totally open with you, I also have to admit that I do have a thing about pubic hair and I love using my clippers to trim and shape my patch.) Arriving at the unit I was shocked at how messy it was. Janice lived in a small 2-bedroom unit which was barely furnished. My new 'girlie' friend opened the door sheepishly and I was disappointed to see that he James was dressed in that daggy outfit of his and had tried his best to look feminine. He offered me a glass of wine and we started to make small talk. The way he was dressed did nothing for me. I just had to start his transformation as soon as possible. Impatiently I asked him to show me his collection of clothes. Excited, Janine took me into his bedroom, where he proudly displayed a wardrobe full of women's clothes. I nodded pleasantly as he pulled out his favourite dresses, but secretly I was not impressed. By the end of this 'show and tell' session, I had made a mental note that most of the stuff would have to go. He did however, have a good selection of ladies underwear and a lovely French Maids uniform. Like the rest of the house, the bedroom was in a mess. First thing to do was a bit of housework, so I ordered Janine to starting cleaning up the bedroom. As I watched him feverishly working, I realized how much he was enjoying himself cleaning the room, wearing his dress. I also discovered why he insisted on wearing the spotted dress, for every time he moved, the soft flimsy material billowed around his stocking legs. Then, after about 20 minutes of him swishing around, I deemed the room presentable. I ordered Janine to strip to his underwear. He went bright red, totally embarrassed. "Strip." I repeated, raising my voice. "But why?" "You want to dress like a woman, look like a woman and possibly act like a woman. To do that, we need to start from the skin up. So Strip!" I knew that I sounded annoyed, but I did not want Janine to back down. I was starting to feel that I had power and I wanted him to do what I said. "Now hurry up and take off that yucky dress." Reluctantly, Janine climbed out of his dress and let it drop to the floor. He stood there in his white nylon full slip, with his pink matching bra and undies reflecting through the opaque material. "Strip off to your panties." I ordered. "Hurry up." As he peeled off the rest of his clothes, it hit me that I had set myself a huge task. Janine had a well toned body, with only a minimal rim of puppy fat around his waist. The main problem was that he was covered in body hair. Thick bear fur!!!!! It truly was a scary sight !!! It was difficult to look at his beautiful pink bra that was sitting in a sea of wavy hair!!! As I looked at his legs, still encased in his thick black, Lycra stockings the swirling pattern of his leg hair was also visible. "Shit, Janine." I don't normally swear, but this sight was pushing the boundaries. "You are joking. How can you even think of putting on a dress with all that fuzz." I was humiliating him, but I did not care. I went up and pulled down his panty hose, all the way to his knees. I felt ill, as his legs were just as bad as his chest. A wave of fear then started to rise. I was getting scared, that feeling of being sick hit my stomach. It was that feeling I got as a youth when ever I was on a date with a guy and the heavy petting started. It was at that stage that I wanted to run. I looked down and to my amazement noticed that Janine's panties were expanding. The front was growing and he was left with a large tent pole, pushing out his knickers. I gave up with men just after I started nursing, for I found that rather than being attracted to the opposite sex, I found the idea of sexual intercourse repulsive. (Sorry to offend.) I then did something that changed my life. Fighting my fear and loathing, I picked out my clippers from my bag and slammed then down on his erect penis. He yelped out, his shaft retreated and I knew then that I had real power. Looking at my electric friend, I knew that it was going to get a good workout today. As I went to move Janine into the bathroom, I knew that my outfit was totally inappropriate for what was needed to done. The only thing that Janine could possibly have for me to wear, would be the French maid's uniform. When I asked him could I wear it, there was movement again in his panties. I was rather pleased with my power, so I let him have his little moment of pleasure. I took out the black satin uniform and held it up to the light. One look at the white stain on the skirt made me change my mind about wearing this outfit. (Mental note: I need to get my own one.) "No good?" He asked as I returned. "Let's go to the bathroom," I answered sternly. "I got some work to do." "What do you mean?" "I am going to get your skin as smooth as the day your were born..." I started to playfully pull on his chest hair. "This is coming off." "No way," he said defiantly. I grabbed a handful of chest hair. "You better let me do this or I'm out of here." I had raised my voice and was now staring straight into his watering eyes. Slowly I started to twist my hand, pulling on the hair. "Alright, alright." He whimpered. "Good girl." And I hauled him into the bathroom Standing him in the shower- bath, I used my clippers on a zero blade to slowly buzz his chest, armpits and legs. The shorn hair tumbled and floated into the tub like little feathers. I've shaved men before, as part of the procedure of getting a patient ready for a surgical operation. This was so different. I must admit that nothing could have prepared me for the thrill I was starting to experience. As I moved the clippers all over his body, I was amazed at how much hair was gathering in the bath. (Mental note. Must not wear an evening gown, when I do this again.) A wet patch formed on the front of his panties, at the tip of his bulge, and a few curly tuffs stuck to that area. I was, at this stage beyond caring. I don't think he knew, how wet I was getting. It fact I was desperately trying to rub my thighs together: a difficult thing to do while standing and trying to shave someone. It took a fair amount of time to totally denude Janine. I was working slowly to avoid dispatching too much hair over me and the bathroom. Finally I was finished and I had to smile as I stepped back to admire my handiwork. Janine was shocked into silence. He just stood there, passively as I had my fun. He looked so much thinner and cleaner, even thought his body was still covered in short stubble. I got the feeling that he could have burst into tears if I so much as said or did anything nasty. I just chattered away, telling him how pretty and lovely I was going to make him. A pulled out a plastic supermarket bag which was at the bottom of the sink cupboard, and handed it to Janine, ordering him to gather up his hair. That was a another laborious job, so I went through the cupboard and grabbed a couple of new razors and a can of shaving cream. "Nice and smooth now," I laughed as I gave him the stuff. "Just think, once you have shaved of all that icky fluff. I might let you become my sissy." He pulled off his panties and I saw how big his shaft had become. It was no longer a worry to me. I was in control and that was my fix. "Now, I have a special reward for you once you are soft and smooth." I slowly closed the bathroom door. "Nice and smooth dear... And when you come out I suggest that you wear a condom, or else you will be washing a few pairs of panties by the time we finish." Back in the bedroom, I was on a euphoric high and as horny as hell. My vagina was aching and engorged, desperate to be touched. (Later, I had to remind myself. Later Lisa.) As I opened the suit bag, the pink bridesmaid's dress exploded out of the plastic. Carefully I arranged it with a new pair of stockings, a full slip and ladies underwear out on the foot of the bed. It was a beautiful frock and I could not wait to put Janine into it. I now impatiently had to wait for my sissy to finish in the bathroom. It was now my turn. The heaviness in my vagina was getting too much, and I needed to be touched. There was no way I was going to let a man do that, so I sat on the bed and started to service myself. I slowly pulled up my dress and let my right hand glide into my wet G-string. I was gushing my now, with my musky syrup well and truly creaming my clothes. Slowly, so slowly I flicked my pleasure bud and even that was just too much. Within seconds I was heavily fisting myself, dragging my fingers in and out of my gaping vagina. I tend to start to phase out as I get excited and almost hit the unconscious state when I finally orgasm. A couple of girlfriends have noted that I "glaze over", so when I'm in full flight, I am sure that a bomb could go off and I would not notice. I was laying sprawled out on Janine's bed, with my dress hitched up, and my hand working hard on my crack, when the sissy walked in. The waves of orgasmic shudders rushed through me and as I started to enjoy the calm of the ebbing tide, a loud cough broke the peace. Slowly opening my eyes, I saw Janine standing by the door, frozen in disbelief. "What?" I snapped breathlessly, pulling down my dress. "Can we do it together?" he asked sheepishly. Dazed, but feeling well satisfied, I laughed that I would cut his penis off if he brought anywhere near me. Then I realized that he did not know that I was gay. I know I was then mean and nasty to my sissy, but I took great delight in telling him that I was "lipstick" lesbian and had absolutely no interest in him. To me he was just a new form of stimulus, just another way in which I could get wet. His panties went flat. I continued by informing him that he was my Sissy and that he would have to do everything I told him to do. I would now be in charge of his wardrobe and I expected him to wear the sissy and girlie clothes that I tell him to wear. I then noticed that the bulge in his panties return, complete with a new wet patch at the tip. There was an uncomfortable silence, as a new wave of orgasmic dizziness hit. "Do you have a spare condom?" Janine asked almost crying. That made me laugh, breaking the ice. "Dear Sissy Janine," I mocked. "You are more likely to get one from a nun, than you would from me. Guess what, I don't really have a need for them. Here used this." I picked up my handbag from the floor and threw him a pad. Sheepishly, Janine picked up the sanitary napkin and just stood there confused, waiting for instructions. "Strip out of your sticky panties." I ordered as I climbed off his bed. I re-arranged my self, still feeling wonderful. I walked past my sissy and went into the bathroom to wash my hands. I was so tempted to lick my fingers, to enjoy my taste, but now I needed to show some self control. (Something I'm just not good at.) I examined his freshly shaved body. It was the start of his humiliation. There were a few nicks, especially on the legs, but generally he had done a good job. His skin was so smooth and it looked so clean. I noticed that he had left his pubes intact, but I did not care, that would be fun for another day! I walked behind him and without warning put my hand between his legs and gently cupped his ball sack in my warm hand. His shaft stiffen and I could feel it almost double in size. "One, two, three," I whispered and squeezed and twisted his scrotum as hard as I could. Janine screamed and dropped to the floor, nearly dragging me down with him. "Naughty sissy", I laughed. "From now on I will tell you when you can get it up." Poor Janine was sobbing from the pain and rolling on the floor, trying to fight the waves of dry retching that were contorting his body. I let him lay there for a good five minutes, amused at the discomfort I had caused. "On your feet, Sissy". I ordered, playfully kicking him with my stilettos. He was still in pain as he pulled himself off the floor. "That's better," I smiled, poking at his non existent penis. "Now dear Janine, I've got you a wonderful present." He just stared, clearly not understanding that this pink dress was meant for him to wear. Picking up the pair of silky knickers and I nodded for him to take them. Slowly he put them on. I made sure that he tucked his manhood back into his balls, wedging the pad over the tip and onto his panties. I held up the bra, and he fed his arms into it. It was a thrill putting on the bra over his freshly shaved chest and pushing his soft chest flesh into the cups. By making the back strap tight, small pseudo girlie breasts were formed. I ran my painted nails across the satin cups and slowly squeezed and twisted each of his nipples. (Not to cause pain, but just to tease.) I knelt down at his feet and worked each of the stocking legs, over his feet. The soft, sheen material slid up so smoothly, because there was not a hair in sight. His legs were as soft and sensual as any girl that I had been with in the past. I made sure that I patted down and straighten out the nylon, especially around his inner thighs. I could feel him shudder, but the way his shaft was positioned, there was no way it could flop forwards. A white full nylon petticoat, slid over his body again like water and hugged his hairless body. I got him to pirouette and watched, smiling as my sissy enjoyed the way his short skirt flared out as he turned. "Now my dear," I whispered in his ear. "Let me make you a sissy. It is time to put on your new dress." The tension, was high both of us. Janine stiffening member was wedged back and frustratingly untouchable for him, while I was oozing sweet nectar and soaking my pad. I unzipped the dress and opened it up. Gingerly he stepped into cloud of pink material. The taffeta rustled and swished as I pulled it up over his hips. Janine lent forwards slightly and put his arms into the bodice. With me now behind him, I was able to pull the material onto his chest. The zipper ran up the back from his waist to the Peter Pan collar and closed the dress snuggly around his chest. (Mental note, I must bring a padlock with me so I can lock my sissy into his dress.) I fluffed out the skirt, evenly arranging the yards of material to sit out like a bell from his waist. The sash was then tied in a gigantic bow, which sat on the bridge of his backside. He looked a picture, as I knelt down again and slipped on a pair of dusty pink, patent leather court shoes, with 4 inch heels. Silly me, but at that stage I really wished that Janine was a genuine female, as I badly needed someone to have sex with. "Right now, Sissy, curtsy to your mistress." Janine fumbled about and ungracefully dropped to his right knee. "Bow your head and look at the floor!" "Next time I might let your wear a wig." I was now running my fingers through his short hair. "But then you are a man and your short hair does emphasize this point." I could feel his body quivering under my touch. Then for some unknown reason I started to call him names and verbally tease and humiliate him. It was getting too much, I was getting dizzy. I moved to the arm chair opposite his bed and sat down heavily. I hurriedly pulled down my knickers and lost control. The pressure was just too much and my aching vagina was given instant relief as my hungry fingers plunged deep into my very soul. Fingers glided in with my vagina relaxed, then fingers out as I tighten my pelvic floor. My hips moved to my pumping rhythm. Again my fingers glided in with my vagina relaxed, fingers out as I tighten my pelvic floor. Again and again and again and again ... And that is how it all started for me. That's how I found my sissy.