True Tales Of Submission And Cross-dressing : Chapter Two - William free porn video

Introduction ------------ Following on from my first instalment, here is another true story. As before, I have tried to remember events as accurately as I can, but of course all speech is paraphrased. I hope there are people out there who enjoy reading this, and perhaps it will inspire people to go ahead and indulge their fantasies. Whatever your kink, there's probably someone out there who will be into it too, and it's not a crime to enjoy life! Curiosity... ------------ So to recap my first instalment - I had been cross-dressing since my teenage years, trying on my mothers and sisters clothes when I was home alone, and even putting on makeup now and again. And in my early twenties, I'd been involved with a dominant woman who encouraged my cross-dressing - in fact, she enforced it. Although that sounds like a dream scenario, the reality took its toll on me, and I was eventually scared off when she wanted me to have sex with a man. Since then, I had started buying some of my own female clothing. I started off by just buying some lingerie... a black basque with thong and stockings, a white bra/panties/suspenders set, and a couple of other bits and pieces. I started getting really into it, and I loved the thrill of trying on some new clothes for the first time. I was living on my own by now, so nobody would get curious about various parcels arriving for me. I bought a couple of skirts, some blouses, one or two dresses. Soon after that, I got a wig (a cute brunette bob-cut number), and started taking photos of myself... just for fun. I was really pleased with the way the photos came out. I was only in my mid twenties, and I am blessed with a slim figure - and frankly I looked better as a girl than I did as a boy. I started ordering items of makeup, and a couple of pieces of jewellery too. The photos were looking great - I would edit them a little bit, to make my face look less blotchy, and blur out body hair... but I didn't really consider it cheating. It was still me. It would have been a shame to keep the photos to myself, but obviously I couldn't show them to anyone I knew. So I decided to post a few online, on a personals site. I wasn't necessarily looking to meet anyone, I just wanted people to see my pictures, and hopefully receive a few compliments to flatter my ego! My profile received a bit of attention, and of course I got a few mails. Most were from guys, dull one-liners asking for my phone number, or whether I wanted to chat online. It felt really weird at first, hearing from men who were lusting after me - many of whom were double my age. I was straight, after all... but I have to admit that it was fun to string them along, flirting back in the hope of fishing for further compliments. I will admit that I loved the attention, it was in stark contrast to any miserable attempts I'd had at meeting women over the years. It was great to be on the other side of the fence for once. Naturally, I did start to wonder what it would be like, meeting up with a guy. What would happen? Actually the thought of being fucked by a man didn't seem as unsavoury as it had done previously, but the thought of kissing a man, or having to suck a cock... urghh. But now and again I would fantasise about what it may be like. When I was dressing up at home, I would sometimes imagine being with a man. I still didn't think it would be something I ever went through with, but I was becoming curious. It was confusing, as I still knew I was straight... I never saw a man and thought to myself "wow, they're hot" in the same way that I did when I saw a cute girl. But still, it was an interesting thought and it added a new dimension to my dressing up. I never told any of my admirers my name. It didn't seem appropriate to tell people what my "male" name was, and neither did I want to use the "female" name which my former Mistress had given me. So I just called myself "j" in all communications. I'd seen profiles of TVs with ridiculous pseudonyms like "candy," "tammy," "nikki," "cindy," etc... but that wouldn't have suited me. I decided that "j" sounded mysterious, so I stuck with that. There was one guy I had been chatting to online - his name was William. He was quite experienced with cross dressers and TVs, and he suggested that I went round to his place and dressed up. He said that we could take things very slowly if I wanted, but nevertheless he would be in control at all times. I could take a selection of clothes with me, and enjoy dressing up in the company of someone who would appreciate me. It sounded like a good idea, and an ideal opportunity to test the water without committing myself, or getting into anything I wasn't comfortable with. I imagined I'd just go round there, dress up, we'd talk and have a drink. Maybe he'd give me a little spank or something, but I could handle that. We arranged a date to meet, and he gave me his address along with some brief instructions: -He did not want to see me in my male clothes at any point. -I was to arrive at his place at 7:30 prompt. -He would buzz the front door open for me, and he would then leave the door to his flat open. -I would let myself in and go into the first bedroom on the right, which I could use to get ready. -I could take as long as I needed, and when I was ready, I was to knock on the door to his study, at the end of the hall. -I was to wear high heels at all times while in his presence. Preparation ----------- The morning before our meeting, I started preparing - there was a lot to do. I ran myself a hot bath, and proceeded to shave my legs. I had never shaved any of my body hair before, so I was slightly nervous about it. Would people notice? How long would it take to grow back? Nevertheless, I continued shaving until they were totally smooth. I then did the same with my armpits and chest. Luckily I do am not very hairy, and don't have much hair on my arms or back, otherwise this could have been a very challenging exercise! When I had finished, I patted myself dry and rubbed moisturiser into my body. The first thing I noticed was my skin was much less sensitive than before. It was a strange feeling, I felt almost numb at first, and not quite what I had expected. Still, I decided that it felt pretty good, and my legs in particular looked fantastic! Next, I started painting my toenails. I had done this before, but I was not very good at it... it took a long, long time to get them looking good, but it was worth it. I loved the look of my painted toenails at the end of my smooth legs. I put a toe ring on one of the smaller toes, which made my feet look every more sexy. I would, of course need to paint my fingernails, but this would have to wait until I arrived, after all, I couldn't travel there with bright red nails. It was time to pack. I took a sports bag, and put all my lingerie in it, and a selection of stockings. By this point I owned 3 skirts - a black suede mini, a short white pleated skirt, and a smart beige skirt - so I packed them all. I then packed all 3 of my blouses, and a black shirt-dress (note - I highly recommend a shirt-dress for situations where you may need to get undressed easily). I also packed my wig, my only pair of shoes (black court shoes with a small heel), some cheap perfume, and my modest collection of makeup. I made sure I had some nail polish remover, and my razor with a fresh blade, so I could shave before doing my makeup. I ate my lunch, and spent the afternoon sitting around the house, nervously waiting until it was time to go. Arrival ------- I arrived at the address slightly early. It was an impressive street in west London, with expensive cars parked as far as the eye could see. I was still driving the same crappy car I'd bought when I started my first job, and it certainly looked out of place in this upscale neighbourhood. I was trembling with nerves, so I took a few minutes to catch my breath... listened to some music and drank some water to try and calm down. When it was 7:30, I walked up to the apartment building, and rang the bell. "Yes?" "Hello... erm... it's me." "Come on up, you know what to do." The buzzer sounded and I pushed the door open. My heart was pounding, and I felt extremely nervous, but I never thought of turning back. I walked up the staircase, and sure enough, William's front door was open. I walked in, shut the door behind me, and walked into the small bedroom on the right as I had been instructed. I opened my bag, and laid out all my stuff on the single bed. There was a lot to do, so I had to get moving. First thing, I went into the bathroom next door to have a shave. I shaved as closely as I could, pulling the skin tight, and going over some parts of my face several times. I also had a quick check for any bits I'd missed on my legs and chest, before painting my nails. My hands were shaking, and it was hard to get them looking anywhere near decent, but I tried my best. I was using quick-dry nail varnish, but it was still taking ages to dry... over 10 minutes before I was able to do anything else! I hoped that William didn't mind me keeping him waiting. I'd decided that I should dress quite conservatively, at least at first. I was still very nervous about the idea of a guy seeing me all dressed up, it would only be worse if I went in there in a tiny miniskirt. I put on my white thong, bra and suspender belt, and a pair of tan stockings. It felt amazing, sliding the stockings up my smooth legs. It is a hard feeling to describe, so sensual and luxurious... glamorous, even! It felt feminine. I did up the suspenders, and then put some small false breasts into my bra. It was time to do my makeup - I was a novice, but tried my best. A thick layer of foundation went on first, and I worked it around my face with a small makeup sponge. I put on some pink eye shadow, which in retrospect must have looked awful, but I thought it was OK at the time. I didn't have any mascara or eyeliner, so the only thing left was my bright red lipstick. I put on several layers, soaking up the excess with a tissue in between applications. I took my wig, and pulled it into place. I stood in front of the mirror - I was quite pleased with the way I looked. The white underwear with the tan stockings looked sexy, but also had an air of innocence about them. I put on my pink blouse and beige knee-length skirt, and finally my shoes. I remembered that William had told me to wear high-heels at all times, I hoped that these would be high enough for him. I actually found it kind of hard to walk in the shoes, even though they only had a modest two inch heel. I finished off the outfit with some basic jewellery: some clip-on earrings, a necklace, two rings and a bracelet. The time had come. I took one last look in the mirror, straightened my wig, and headed down the hallway to his study. I knocked on the door, and tried to hold my composure. I heard his footsteps coming towards the door... it probably only took five seconds, but it was the longest five seconds of my life. The door opened, and I saw him for the first time. A well built, middle aged man, with grey hair and glasses. He was well groomed and smartly dressed. He had an air of confidence about him, which I picked up on straight away. "So, miss 'j'... come on in." I walked into his study... trying to walk confidently in my heels as best as I could. "Welcome! It's nice to meet you at last." "Thank you," I replied nervously. "Let's have a look at you," he said as he grabbed my hand and pulled me towards him. He put his hands on my shoulders and too a good look at me, from head to toe. He turned me round, and gave my bottom a gentle pat. He then reached down to the hem of my skirt, and I felt his hand on my leg. He started lifting my skirt, stroking my thigh through the stocking as he went. My breathing became heavy. This whole situation felt surreal - here I am in a stranger's house, dressed in female clothing... letting this man put his hands all over my body! It felt very wrong, but that's probably why it felt so exciting. And my excitement became quite visible. His hand rose further, up to the top of my stocking, which he briefly played with. "Good," he said. "Glad to see you're wearing stockings and suspenders." I remained silent, too terrified to really say anything. He pulled up my skirt further, revealing my bottom. "Hmmm," he said, as he admired my rear, and toyed with my skimpy white thong. He rubbed his hand over my bottom for what seemed like eternity. I didn't know what to do, I wasn't sure if I was supposed to respond in some way. I just stood motionless while he touched me, in ways which I had never imagined I would be touched. First kiss ---------- He took me into the kitchen and offered me a drink. I had a choice of either white wine or a Bacardi Breezer. I chose the white wine, while William poured himself a beer. We went through to the lounge, where we sat together on the sofa. We chatted for a while, about various things. He told me about various "girls" he saw now and again, and we discussed the possible reasons why I liked about dressing as a girl. I felt very self conscious, especially when I spoke. I wasn't sure if I was supposed to be attempting some sort of female voice, but I knew that I wouldn't be able to manage one. So I decided that just speaking slowly and quietly - almost under my breath - was the best tactic. He put his hand on my knee while we were talking, and gently stroked my thigh from time to time, which I liked very much. After a while, he told me to stand up. I obeyed, and we both got up from the sofa. He grabbed my arms, and held them tightly against the side of my body. He was a strong man, much stronger than I was. He moved closer towards me, until our bodies were against each other. He was going to kiss me. I didn't know what to do, I hadn't even imagined that this was going to happen. I felt so naive. Should I tell him to stop? Should I push him away, and say that I'd made a mistake? I did neither of these, and just stood there, frozen with fear. I closed my eyes, and felt his lips touch my own. A short, soft kiss at first. And then another one. Oh my god, what was I doing? I had become hard, and I could feel that he was too, and that just made me more terrified... absolutely terrified. But it felt wonderful. He kissed me again, and he pushed his tongue between my lips. I accepted his tongue into my mouth, but did not kiss him back at first, remaining totally passive. He pulled me closer, pulling me into his body, while his hands explored my thighs and my bottom. He paused briefly, and undid a couple of buttons of my blouse. He played with my bra straps for a few seconds, before undoing the remaining buttons. He told me to stand still. He walked out of the room, and came back a few seconds later with a camera. He started taking pictures of me, in my now half-undressed state. I didn't know what to do... of course I was not used to someone else taking pictures of me like this. Again, I just stayed passive, not moving unless I was told to. He came back towards me, and put his hands on my waist. With my blouse unfastened, his hands were now caressing my bare flesh around my waist and lower back. He pulled me towards him and we kissed again, this time I put my hands around his neck, and kissed him back. It felt instinctive, and natural in a strange way. I stroked his neck and face, as he pulled me in tighter and put a hand up my skirt, feeling my stockings and underwear, before touching the area around my anus. He pulled back, and looked me in the eye. "I'm going to fuck you," he said to me. "I... I... not sure" I stammered an attempted response. "I'm going to fuck you," he repeated. "I'm going to keep you here for the night, then I'm going to fuck you again in the morning." I nodded, and looked down in acceptance. I knew deep down that I wanted this, so I decided at that point that I would let him do whatever he wanted with me. I would give myself to him for that night, completely handing over all control. He put his hands on my shoulders, and pushed me down onto my knees. He unfastened his trousers, and let his trousers and boxer shorts fall to the ground. He put a firm hand behind my head, and pulled me towards his cock. I felt the tip of his penis against my lips, and gingerly kissed it. I then started to slowly lick it, before finally taking his swollen cock inside my mouth. He pulled my head towards him again, forcing his cock to the back of my throat, and my nose and lips into his pubic hair. I gagged, and struggled for breath, but he held me tight, before eventually pulling out a little bit. I started to rub his cock, but he told me not to. He didn't want to climax yet... he wanted to save himself for later. So I just used my tongue and lips, and tried to remember what I had liked when girls had given me blowjobs previously. He reached for his camera, and told me to look up at him. He took several photographs of me, with his cock in my mouth. It felt humiliating, but I liked it. It made me feel like a bit of a slut. When William had had enough, we sat on the sofa for a bit, and kissed for a while. He then suggested I got changed. He handed me a brand new pack of black lace-top stockings, and a pair of red 4 inch stilettos, and told me to put on some lingerie which would go with them. So I went back to the small bedroom, and put on my black basque. The stockings he had given me were very good quality, they felt beautiful as I slid them onto my legs, and the lace detail was very pretty. I put on the shoes, and walked back to the lounge as best as I could, holding onto whatever I could use to steady myself! William was waiting for me with his camera, and took a few shots of me in the underwear and stockings, tottering along in the red stilettos. Venturing out ------------- "I'm going to take you out," William said to me. I was pretty terrified at this prospect. "Where are we going?," I asked. "Just to a bar I know. And maybe a club too. I want to show you off. I want people to see us together, and to see that you are my girl." "OK," I replied. After all, I had already made a decision to just go with the flow, and do whatever William wanted. He made a phone call to a friend of his. He said we were going to a place called The Philbeach, and that he was with a girl... "a B+." I wasn't sure how I felt about being described as a B+. It would have been nicer to be an A. But it was quite a turn-on, being talked about in that way... like a piece of meat, and besides: in retrospect, given my makeup skills at the time, B+ was probably quite generous. I put on my black miniskirt, and the same pink blouse I had been wearing earlier. Most of my lipstick had rubbed off when I was sucking William's cock, so I fixed my makeup as best as I could. We left his apartment, walked down the stairs, and out into the cold night. The first thing I noticed was the breeze on my legs - it was a very strange sensation. My skirt was so short that I could even feel the breeze against my genitals, and when I walked the tops of my stockings were clearly visible. Basically I was dressed like a slut. But somehow, being with William, and letting him take control, made me feel relatively confident. It felt like it was out of my hands, I had no choice about walking down the street dressed like this, so there was no point worrying about it. In some ways it felt as if I was observing events as a third party, it didn't seem as if this person was me. It didn't seem real. William's car was a Mercedes SL class - an expensive sports car. He held the door open for me and I tried my best to get in with some amount of dignity, but my skirt rode up, showing at least an inch of my suspenders. I realised that I would probably be spending a lot of the evening adjusting and pulling my skirt, in an attempt to preserve some level of modesty. The bar was not far away, and was in the basement of a gay and TV friendly hotel. William left me in the foyer, while he went to park the car. I started to panic slightly at this point... being left alone in this strange place was very intimidating, and a wave of relief came over me when William returned. I felt safe when he was with me, without him there is no way I would have had the confidence to come to a place like this. The bar was not busy - probably less than ten customers in there. Two rather old trannies sitting together and chain-smoking... a man in a suit... a couple of American guys enjoying their drinks and having a laugh about something... a fairly good looking blonde sitting at the bar. We sat at the bar also, and William ordered me a gin and tonic. It wasn't something I'd usually drink, but it seemed appropriate, and tasted great. I wondered if my clothes were somehow affecting my taste buds! William's friend came into the bar - another smartly dressed middle aged man, and he was with a "girl" also. She has a good figure, and was wearing a tight mini-dress. I was introduced simply as "j," and we chatted for a while. It turned out that she was a car mechanic by day, and spoke with a deep voice in a strong Birmingham accent! I glanced around the bar, and the guy in the suit had struck up a conversation with the blonde sitting at the bar. Another one of William's acquaintances came and joined us. He looked and sounded Mediterranean, possible Greek or Turkish. He seemed to like me, and kept on putting his arm round me, and touching my bum. He was a bit creepy, but I did like being the centre of attention. He even suggested that if I get bored of William, I should go home with him instead, but William stepped in at that point. "Hands off," he said with a grin. "This girl's mine tonight." Another gin & tonic came my way. I decided that I could get used to having drinks bought for me all night. The bar was slightly busier now, but still fairly empty. The guy in the suit and the blonde had moved to a sofa, and were kissing... they certainly hadn't wasted any time, I thought to myself. William suggested that we went to a club he knew. We all agreed - there wasn't much happening in this place. I waited in the hotel foyer for William to get his car, while his friends left in another car. It was at least a 20 minute drive, the club was right at the other side of town, over in East London. I felt slightly vulnerable in the car, but it was dark outside and I felt reasonably sure that nobody would notice me. But so what if they did? Whenever we stopped at traffic lights, William would reach over and touch my legs, or put his hand up my skirt. I liked being toyed with like this. Eventually we parked near to the club, and we got out of the car. William paid for us both to get in - after all, I did not have any money with me. No wallet, no keys, no phone... it's a good job I wasn't planning on running away. There was a real mixture of people in the club. Probably about 50% "girls" and 50% admirers, from all age groups. Some of the girls looked great - very elegant and feminine, with really good makeup and sense of style. There were quite a few Asian girls, and a few girls who had obviously had surgery. William told me that quite a few of them worked as escorts, and this is where they came on their night off. I had never been attracted to transvestites or transsexuals before, but I had to admit to myself that some of these girls were really hot. Of course, some of them did not look so great. There were a few middle aged guys in floral dresses who frankly looked quite comical, but they were having a good time. It was an accepting environment, and they had as much right to be here as anyone. William got me another drink, and then left me alone while he went to the gents. I was feeling quite drunk by this point. I noticed that a few guys were checking me out. I liked the attention, but I wished I was wearing a slightly longer skirt! One guy came up to me, he was probably in his mid twenties - about my own age. "What's your name?," he asked. I wasn't quite sure how to respond. "Erm... J," I replied. "Jane?," the guy asked. "Yes," I nodded. It was easier. "I like you," he said, as he put his arm round me and lent in close. Wow, I was already being hit on after just a couple of minutes. "Sorry, I'm with someone," I told him. He was a bit creepy, I wanted to get rid of him. "Where are they?," he asked. (ha, men! They never take no for an answer!) "Just in the toilet. I'm sorry, I came here with someone." He left me alone after that, and to my relief, William returned soon after that. I was glad he was there, I decided that I was in no way ready to come somewhere like this by myself! William's friends arrived shortly afterwards, and they chatted for a while... making small talk about their businesses, and pointing out girls who looked particularly good. There was another round of drinks, and by now I was really quite drunk, and my legs were getting tired standing in heels. William turned to me and said loudly- "I think it's time I took you home and gave you a good seeing to." He wanted people to know that he was going to take me home and have sex with me, and he possibly wanted me to feel a little humiliated. Being used ---------- William held my hand, and lead me into his bedroom. He pulled me against his body, and kissed me deeply. We embraced, and I could feel his hard cock against my body. He undid the buttons on my blouse and the removed it, revealing my lacy black basque. He then unfastened my skirt, and let it drop to the floor. He pushed me onto the bed, and he lay on top of me, holding my hands above my head. He continued to kiss me, his tongue probing deep into my mouth. He got up off the bed, and walked over to the wardrobe. He took out a large bag, and from within the bag he took two leather restraints. He came back to the bed, and tied my wrists to the metal bedstead, with me still lying on my back. He then took out a blindfold, and put it over my eyes, so I couldn't see a thing. I could hear him taking his clothes off... he was undoing his belt... taking off his trousers... taking off his watch. A pause followed. I realised that he was taking more photos of me. He returned to the bed, and lay next to me. I could feel his naked body next to mine, and he started to touch me. I lay still... well, I didn't have much choice. He moved on top of me, kneeling with one knee either side of me. He moved up towards the top of the bed, and propped up my head with 3 or 4 pillows. He told me to open my mouth, and he put his cock inside. I licked and sucked, as he slowly thrust back and forth. His thrusts got faster. I struggled for breath, as he started to fuck my mouth, deeper and harder. His cock was practically entering my throat, I was trying not to gag but it was impossible. Every minute or so he gave me a short rest to catch my breath, before starting again. He grabbed my head and pushed his cock all the way in, I started to panic, before he eventually withdrew. I could hear him rummaging in the bag again. He came back to the bed and put a ball gag in my mouth, and fastened it behind my head. He took the fake breasts from out of my basque, and clipped something onto my nipples - I since discovered that it there was a small clamp on each nipple, attached to each other with a chain. He unfastened my suspenders, and took off my thong, before fastening the suspenders again. He then grabbed my ankles, one in each hand. He pushed my legs up into the air, and rested them on his shoulders. He took his time, stroking my legs, and my buttocks, before he started touching my genitals and my anus. He pushed my ankles back further still, and one at a time he tied them to the bedstead, close to where my wrists were. I heard a click as he opened something, and then I felt the cool gel being rubbed around my hole. He then took a butt plug - or perhaps a small dildo - and started trying to work it inside me. Slowly at first... he pulled my buttocks apart, and expertly guided it forwards, into my hole. I moaned into the gag, as he started to pull it in and out. He grabbed my hard cock with his spare hand, rubbing it... but not enough to make me climax. I don't think he wanted me to... I was there for his satisfaction, first and foremost. He slowly pulled the butt plug out, and positioned himself in front of my hole. I felt the tip of his penis against me... he started to push slowly towards me, I moaned as I felt myself stretching to accommodate him. He shifted his weight so he could push forward with more force. His cock was quite wide, it had certainly filled my mouth earlier on... and now he was inside me. It was certainly painful, but I was enjoying it. He started with small thrusts, and with each one I let out a short whimper of pain and pleasure. His thrust got harder and faster... I was still blindfolded, so could not see his face... but I heard his moans getting louder. My whimpers had turned into small screams. If he hadn't gagged me, the whole neighbourhood probably would have heard! Although I was loving being used like this, I wasn't sure how much more I could take. It felt like his cock was going to tear me apart. Eventually he climaxed, and after he withdrew, he lay on top of me and kissed me passionately. I had been totally passive throughout the whole thing. He had treated me like some sort of toy, like a human sex doll. He had used me, and it had been thoroughly humiliating. It had been wonderful. He untied me, took out my gag, and took off my blindfold. He went to the wardrobe and took out a black nightdress. He told me to put it on, and to get in bed. He turned the lights out, and got into bed with me... he put his strong arms around me, and I fell asleep. ------------ When I woke up, initially I wasn't sure where I was. I soon realised that I was wearing a nightie... jewellery... my wig was still on. I looked over and William was next to me. He woke up shortly after me, said good morning, and gave me a kiss. He went to the kitchen to get us a glass of water each, then returned to the room, briefly rummaged around, and produced a length of rope and a box of condoms. It wasn't over yet.