The Skirt Chaser Chronicles: 2. Paul's Story free porn video

The Skirt Chaser Chronicles: 2. Paul's Story: Part One: My name is Paul. I am the product of the best public school education that money could buy. I had always felt, however, that there was something missing from my education in an all boys' school and obviously that was girls. I met Sara a few months ago. She was my first girlfriend. Sara was everything I expected in a girlfriend. She would wear traffic-stopping skirts, mainly miniskirts but sometimes skirts with a slit up the side that would show off most of leg when she moved. She was the most beautiful girl I had ever seen and she was incredibly sexy. So to start with I bought her flowers and things thinking I was on my way to getting laid. Then, however we had THE conversation and she made clear to me that she was a virgin and that she had no intention of sleeping with anyone until she got married but there may be certain things that she would be prepared to do. I had been taught to respect women but I was disappointed. I said however that I understood but I stopped buying her things. After a few weeks I noticed that she had stopped making an effort with her dress but we had gone from dates to a relationship so that did not really matter to me although I missed seeing her in a skirt and I would see other women wearing them and think about what the skirt they were wearing would look like on Sara. Around a month ago Sara seemed to be getting a bit insecure and asked me about our relationship. I recall she said something like, Paul, don't you think I'm sexy? Why do I get the impression I am just a stop gap before you move on to someone else? Why are you always looking at other women?" I could not bring myself to say that I was thinking about the skirts that the other women were wearing and what they would look like on her or about thinking her to be the most beautiful and sexy woman in the room so I told her I loved her and that I was a boarder at an all boys boarding school so generally the only women we saw in a skirt were our mothers and the matron (who was old enough to be our grandmother). I recall I added that now I was out in the big wide world it was only natural that I was attracted by women in skirts. I knew that people always said that all public school boys were gay so I added, Would you prefer I was homosexual like a lot of my classmates and eyed up men?" The truth was I had no idea how many of my classmates were gay but I had my suspicions about a few of them. "No, I want you just for me," she replied. I was relieved because I was worried that she was getting a bit bored of me and might dump me because she had stopped making an effort and wore trousers whenever we went out. I had tried to encourage her to make an effort and to wear a skirt but she knew what she wanted and refused to do so. One Sunday night we were talking in the pub and I tried one of my subtle attempts to get her back into a skirt again. I said "You know I find a young woman in a skirt and pantyhose or stockings attractive but there don't seem to be as many girls around as before I started being a boarder." Sara asked, "Oh really, how many would you say that you see on an average night in the pub with me?" I wanted her to feel she would really stand out if she did without saying so as I could not believe a woman as beautiful and sexy as her did not know she was beautiful and sexy but if she did not maybe that was the reason why she had not dumped me so I said, No more than 3 or 4." I knew I had underestimated the figure I gave about the popularity of skirts but I did not think it would matter until Sara said, Ok. Let's make this interesting. We will come to the pub every night this week. If we see 10 girls tonight you will wear pantyhose yourself until closing time tomorrow. If we see 20 girls tonight you will wear pantyhose on Tuesday too. A girl in trousers allows you to discount a girl in a skirt. The same will apply each day but the score can only carry forward for one day if it is a low score. So say you only saw 4 tonight but saw 7 tomorrow you would be wearing pantyhose from Monday night and for the following day until closing time as the average for both days was higher than your estimate. If then on the Tuesday you only saw one girl for example then you would be entitled to remove your pantyhose that evening after closing time as the Monday night girls had landed you in pantyhose then and would no longer count on Tuesday night but if you had not wound up in pantyhose the previous day the girls would count towards the following day. If on any day you are wearing pantyhose you will include yourself in the "girls in skirts and pantyhose" count and your score would therefore increase by one girl. If you go two consecutive days in pantyhose you will then have to wear an additional item of female clothing the following day if you are to wear pantyhose again and each additional item of clothing will count as a "girl in askirt and pantyhose," If you go three consecutive days you will have to put on a second item of female clothing and you will now count as three girls." I had got myself into trouble and I could not dig myself out of this without admitting my true motivation. I was worried that I might lose on some of the busier nights and have to wear some pantyhose but there were never more than three busy nights in a row so I should not have to wear anything else if I agreed to this and then Sara made an offer I could not refuse, If you go a week without wearing pantyhose I will dress as a French maid before leaving home and accompany you to that seedy pub across the road where I will dance a striptease and I will arrange for you to be allowed to video the entire evening." Wow this would be amazing! "Deal!" I said. I was really eager to see her as a French maid stripper and I did not mind if a few other men saw her. Maybe I might even see her wear a skirt again from time to time. Sara then wrote down the deal and we both signed it. It started well. Sunday night was quieter than normal and we only saw 4 girls in pantyhose or stockings like I said. My fantasy that she would be doing this striptease was a day nearer and I did not look like I was going to have to wear pantyhose. Matters took a turn on Monday night when Sara decided to put on a miniskirt and fishnet pantyhose. So she was taking this seriously but I did not think I needed to be worried as I did not think many women would be out or if they were that they would be wearing skirts during the week. I was excited to see her in a skirt again and I loved her wearing fishnets as they were the sexiest pantyhose out there. I was on the look-out for girls in trousers as we went into the pub. I was keen to see her dress as a French Maid. I also wanted to get my score down from yesterday. Just then a stunning redhead came in wearing a skirt to die for, gorgeous seamed pantyhose and designer stilettos. Then two girls came in together, one in a miniskirt and pantyhose or could I see a garter belt? But this was ok as the other girl was wearing trousers and therefore cancelled her out. Then no-one came in for about another hour. OK so we were on a total of five for both nights as the two girls had cancelled each other out. It was looking good and I thought Sara had decided not to include herself in the score for tonight. Then four girls in St Trinians outfits wearing fishnet stockings came to really mess things up. I saw Sara reach for her bag where I imagined she had some pantyhose for me. "Hey not so fast," I said, "that's only 9! You can't use me to reach 10!" "That's ok Paul I wasn't but I am using you towards Wednesday's score." "What do you mean?" "Paul, you are so busy looking at other girls that you are missing the one in front of you. What am I wearing?" So Sara did want to include herself in the score! "Hey, that's cheating!" I said as I wanted to try to avoid the complete humiliation of wearing pantyhose. Quick as a flash she replied "No it's not! You yourself said you wanted to see me in a skirt and tights. It's simply unfair of you Paul to accuse me of cheating. After all isn't this deal about you getting me to dress up as French Maid? I make an effort for you and you complain!" I tried another tactic to avoid her pantyhose "But you wore trousers yesterday didn't you? So that should be a minus score!" "Paul now that really isn't fair as I did not have the opportunity to change." I had to agree and she then pulled out a present she had bought for me. I held it in my hand and smiled as she took a picture. Then I noticed "Paul's first pantyhose" was written on it. So was confident that this would not be the only time I would be doing this. I was starting to get worried. "Oh you can't be serious!" I said as I realised what she had done and tried desperately to find a way out saying "Can't we just forget it? You have your picture of me smiling whilst holding them. I have never worn pantyhose before and do not intend to start now. That's something that gays do." I did not want to dress in women's clothing and was convinced this was something only homosexual men did. Then she responded forcefully, Paul, are you telling me you are not a man of your word? A real man would not feel threatened by having just to wear one little item of women's clothing. And I know you are hoping to watch someone do a striptease across the road. Wouldn't it be terrible if people didn't keep their words? In fact aren't gay men known more for breaking their word than wearing women's clothing?" There was no way I was having my girlfriend think I was gay. "Ok! How do I put them on?" She told him how to roll them up in a ball and then ease them up my legs. I was not going to do this in the middle of the pub so I went off to the gents to put on the pair of pantyhose that I had just been given. Sara was calling them my pantyhose but I did not want to think of them in such terms. I mean how many men do you know who own their own pair of pantyhose? Certainly ownership of pantyhose is not something that I had ever heard any man I know talk about. I was worried someone would see me under the door to my cubicle as I took my socks off and put the pantyhose on. I had never felt anything quite like this. I tried to put the pantyhose on and then get my shoes on before anyone could see my feet were not in my shoes and wonder what I was doing. In doing this I had forgotten to put my trousers back on over the pantyhose and then crashed around inside the cubicle trying to get my trousers on over my shoes. The outcome of this was that if anyone was watching they would have even more opportunity to observe my pantyhose encased feet as I had to take them out of the shoes and pull my trousers up before putting my feet back in the shoes. What a disaster! Still I had avoided discovery as no-one had come in. It was an amazing feeling wearing pantyhose which I would recommend to anyone even if just once and it set my legs off tingling as if every hair on my leg craved to be touched by this extraordinary material. The pantyhose was really smooth and I had got an adrenaline kick from the whole drama I had just been through. When I came back out Sara insisted that I gave her the socks I had been wearing and reminded me I could only take the pantyhose off on Tuesday night if we did not reach 20 girls by then. As she told me this she rubbed my trouser legs and I think I shuddered partly from the tingling and partly from the thought that Sara new what I was wearing under my trousers. I let her know that she was not going to hit 20 before Tuesday night and I would be free of the pantyhose. Then Monday turned from bad to worse because the St Trinians girls who had been steadily getting drunk had been joined by 10 of their friends, who were all dressed in the same manner and it was still an hour and 30 minutes until closing time. There was no use pretending - I was going to be stuck in these pantyhose until Wednesday! "Looks like you could be in panties by Wednesday Paul!" Sara gloated. I am sure my face betrayed that I was none to happy about that because she then said, No sulking! You wouldn't expect it of me whilst I dance that striptease, so I expect you to try to enjoy this. How does it feel?" "Dangerous," I said. "I feel like someone might find out at any minute and expose me. Then I wouldn't be able to show my face in this pub again! It's not normal for men to enjoy wearing pantyhose." That was a slip. I hoped that she had not noted that I said that I was enjoying it. It was not like I was the sort of man who enjoyed this sort of thing. I did not want my girlfriend thinking I was gay. Then I saw she had this radiant smile on her face. Had she just seen something or someone behind me? "Look Paul! We're being invaded!" she said. I am sure I said something like "Oh no!" in response. This had just become the mother of all disaster as the "girls in skirts and pantyhose" count more than doubled from 21 to 50 as yet more St Trinians girls turned up. She could not have set this up. There were just too many. Then I realised that I was not just going to be stuck in panties but wearing other feminine clothing too! Just how bad could this get? I did not want to see another girl in a skirt ever. I knew that this also meant Sara was not going to be becoming a stripper any time soon. She had correctly predicted how this week was going to work out. She told me I would then have to add a bra on Thursday night and a corset on Friday. I was terrified at the prospect and I believe I was shaking. The pantyhose could just about be concealed but I had heard often enough the phrase "visible panty line" and suspected that people would be able to see I was wearing panties and not boxer shorts, strangely I had never been concerned that people might realise I was wearing boxer shorts - I wonder why? And then there was the bra, even if it was not padded the straps would show through any shirt I had and how on earth was I going to conceal I was wearing a corset? I said something like "I can't believe it!" he said. "You are going to have some time to get used to it!" Sara gloated. "As it looked like you were trying to renege on your word I think it only fair that you give me a pair of your boxer shorts each time you have to wear an item of female clothing other than pantyhose. Consider it your punishment." I was so shell-shocked I know I did not even object and just signed what she put in front of me. Tuesday night at the pub was quiet and we only saw two girls, this time not wearing St Trinians outfits but both wearing black tops and matching miniskirts. The first was wearing fishnets and the second was wearing nearly black pantyhose. "Two is an amazing result after yesterday!" I said. Sara reminded me that I had missed two others - her and me! So we were now at four. She did not seem disappointed that she had not won this evening, I guess because as she knew I was going to be in a corset on Friday night in any event and she had until the weekend before she needed to win again anyway. She did not have to wait long though. Wednesday night giving me what looked like a present and like a fool I smiled for the camera before realising that this time it said "Paul's first panties" on it. How could I allow myself to be mugged like that a second time? I think it showed that I was not happy when I realised what had just happened but I may have got away with it without Sara noticing. As the pub was empty and we could only be seen by people coming in the front door and not the bar staff Sara dared me to stand holding the panties in front of my groin and to look pleased with them as she photographed me holding them. Just as I was doing this three girls came in wearing netball skirts and pantyhose and Sara explained to me that I had just lost Saturday as she watched me quickly hide the panties hoping that the girls had not seen them. "Wait a second how do I lose on just three girls?" "Have you forgotten me again? And in addition to counting me in you have to count yourself twice which means that with the four from yesterday we now have ten! I expect some gratitude for the money I am spending on your wardrobe, Paula." This was too much. Was Sara going to apply to have my name changed next? I said "Now don't start calling me Paula! But thank you for my panties and my pantyhose Sara." I had forgotten that I had yet to put them on but Sara was quick to remind me, Haven't you forgotten that you are now meant to be wearing them? And that you owe me your male underwear?" she said slapping my ass as I started to move past her to the gents. Although there were no further girls that evening I could see this would only het worse as Sara would only need six girls on Thursday to give her Sunday too, as I would be wearing my first bra tomorrow and I would therefore account for three girls on my own. Then on Friday Sara would only need five girls as I would be wearing my first corset and with whatever I had to add on Saturday I would personally account for half of the score without adding Sara! So I slipped on the panties and then pulled up my new pantyhose that Sara had included with the panties as the first pair were getting smelly. Yes I admit it the panties were exciting too and I had learnt from yesterday how to get changed as quickly as possible by hanging my trousers on the door whilst I sorted out putting on the panties and pantyhose. Again it is hard to describe wearing panties to someone who has not save that it made me feel that Sara had me by the balls from the way they fit snugly round my dick and gently squeezed on it. I needed to draw a line under all of this fast I was starting to have strange dreams about becoming homosexual or a professional drag artiste. Why didn't I think of this before? I would pretend to be sick until Monday and be able then to turn up in one of my three remaining pairs of boxer shorts. So I called Sara and pretended I was sick and would not be able to make it to the pub. There was no pulling the wool over her eyes as she immediately responded, Oh that's ok Paula I will go to the pub without you, after dropping off your bra which I expect to see you wearing before I leave. I will let you know the score when I get home but I might add a few girls if it is a slow evening." I could not have that so I said that I was starting to feel a bit better and maybe would try to come out with her. I think with hindsight I would have been better staying home sick as the evening was a disaster for him as soon as I learnt that there was a hen night there. There were twenty six beautiful girls all looking like Sara had invited them in their damn miniskirts so I was stuck now until Wednesday! I was starting to think that if Sara was to become stripper it was unlikely to be happening as a result of this bet. Sara now had more of a wandering eye than I did and seemed to enjoy watching girls in miniskirts, to a point where I was starting to wonder if she was a lesbian. I had to point out to Paul that he wouldn't be out of pantyhose now before next Wednesday at the earliest! Sara had me pose with the bra in the same way as with the panties but out of sight of the other people in the pub. I noticed that someone had sewn false breasts into the push-up bra she had bought me. This made me look like I had really large breasts. As usual I went off to the gents to get changed. I needed a changing room now as I had new panties and pantyhose to match the bra. I really struggled to work out how to put on the bra but in the end I worked out I could attach it in front of me then spin it round behind me before putting my arms through the straps. Sara looked delighted to see me and I assumed my underwear was really obvious so I asked her, Is it really obvious?" Sara replied, Oh no Paul I would have no idea." And then Sara said, Aren't you forgetting to give me another pair of your boxer shorts?" I did as I was told. "Now listen Paula, tomorrow you get to wear your first corset so I expect you at my house early so that we can get to the pub in plenty of time!" I did not respond as I had earlier when she changed my name to Paula as I was starting to wonder if I had been born a girl and was really Paula then had my sex changed to Paul because why else did I find wearing a bra, panties and pantyhose so exciting and why did it feel so natural? Looking down at the bra it felt like I now had real breasts. I really liked the feel of the elastic on my shoulders. The next day at work the boss asked me what I thought I was doing wearing what I was wearing and although I do not know if my bra was more obvious than Sara had said I knew he had either worked out I was wearing it or seen my panty line or pantyhose. He said I should take a few weeks off to "get my head straight". As I had got out of work early I was a good girl and arrived early at Sara's house as I had been asked to. Why was I referring to myself as a girl? Because Sara kept calling me one and it was hard for me to think of myself as anything else dressed as I was. Sara said, Paula this is your first corset and putting on a corset is definitely, as you put it, about making an effort. You will feel pain and I know that as you are a man, Paula..." I interrupted her and said that, I think you will find my birth certificate says I am called Paul." Sara ignored me and continued, "You may find this particularly hard. This first time I am going to lace you into it and this will help your body get used to wearing a corset but it will get smelly after a day so as you are going to be wearing corsets until at least next Wednesday night I will have to buy you a few others." I did not fully realise what women went through being laced into a corset and by the time Sara had finished I had an hourglass figure that many women would even be jealous of and we both needed a drink. On the way to the pub Sara explained to me that I needed to change my drinking habits for the time being and drink something other than beer as she would never get the corset off me and Sara suggested I have a ladies drink like a babycham. I agreed reluctantly knowing that I needed to be able to get out of this corset one day and I guessed a babycham was more appropriate for the sort of customer who wear a corset than the beer that I would rather have drunk. "What does it feel like to be a man in a corset?" Sara whispered seductively in my ear. The way she did it had me feeling like I was somewhere else and I imagined a world where men dressed like women and women dressed like men. Then I came back to my senses remembering I had been asked a question about men and corsets. I don't recall exactly what I said like when you try to remember a dream but I must have admitted that it was surprisingly comfortable once you get over the pain of putting it on and I guess it improves your posture as you are forced into a very upright position I knew also that it really enhanced my breasts. Just then a group of five girls in skirts walked in and Sara said "Wednesday." I had got used to this now and pointed out to Sara "You don't need to remind me I now count for four girls and you are dressed the part too." On Saturday Sara called me on my mobile and said, "It is time for you to walk the walk." "Look I am not wearing stilettos if that's what you have in mind," I said. "Oh yes you are," Sara said. "But I will admit that there is no way you are going to be able to hide what you are wearing on your feet. See you down the pub." When we got to the pub the place was packed. There were around forty girls in skirts and miniskirts. "That takes me through to next week at least doesn't it?" I said. "Remember to enjoy yourself Paula," Sara said. "Would it make a difference if I told you you are not the only man in a corset here tonight?" "No! Are you serious?" I said. Then she dropped a bombshell, I have only noticed four real girls here, but they are all in skirts which carries you through to next Thursdaybut I will agree not to count other men in drag," I said. Suddenly the fact that I was wearing a corset, bra, panties and pantyhose did not make me feel so odd as I now knew that there were other men here who were wearing more women's clothing than I was. I went over to one of the girls and asked her how long she had been wearing drag for. She said she had been doing it for about a year and then she asked Sara the same question and Sara said "About the same" as if there was some sort of in- joke between them. Had I just asked one of the real girls about whether she was wearing drag? Then she introduced me to her boyfriend Rosario and somehow it was like I had known Rosario all my life. I felt at ease with her and told her about how as I had lost my bet with Sara I was going to have to wear stilettos for the first time tonight. Rosario was really kind and told me that Sara had picked out a beautiful pair for me before explaining to me how to walk in stilettos and how I would have to lean forward more as I walked in them and how they would hurt his calf muscles. Sara said, "You will get to feel what I mean when I say that my heels are killing me." Rosario helped me stand up in them and held my hand as I teetered round the room before getting confident enough to go to the gents. Tonight the sign on the gents door was half male and half female. Afterwards I told Sara about how I had been given some time off from work so I would be able to get to her house early each night next week. I sensed that Sara wanted to ask me why I was off work but I did not want to talk about how this week had messed with my head and how I might even lose my job over it. I managed to avoid giving her a pair of my boxer shorts but I knew that by next week I would be running out anyway. The next day Sara gave me a bag of corsets that she had bought for me which I could do up myself as they were front fastening. Then she told me that she would now be starting on my outer appearance so as she had introduced me to stilettos yesterday I would be wearing make-up from now on. I could not argue with this as I knew I would be wearing a dress tomorrow and I would be more comfortable having make-up done first. I wanted Sara to do a good job so I sat still so she could do her best and she also did my hair, which was fortunately quite long for a guy. Then she had me look at myself in a mirror and although I was still wearing male outer garments the make-up and stilettos screamed that I was a woman before you even saw my breasts. She insisted that I give her another pair of my boxer shorts and we went off to the pub. It was busier than the previous Sunday and with me wearing make-up, stilettos, a corset, a bra, panties and pantyhose I now counted as six girls and Sara was the seventh! This meant we only needed to see three girls and there were more girls there than I cared to count. Sara said that there were only fifteen girls and although I was sure she was wrong she pointed out that I was still going to have to carry on becoming a woman until next Saturday. She said I had to bring two pairs of boxer shorts on Monday as they weren't appropriate for me anymore. On Monday night Sara put me in a dress for the first time. I think I looked hot as the landlord insisted on me kissing him and Sara seemed more attentive to me, almost like a man on a first date with a new girlfriend. We then saw enough girls to take us through to the following week and Sara took the boxer shorts from me just before we left the pub. On Tuesday Sara took my last pair of boxer shorts from me and I knew I now accounted for nine girls now. Unless I got lucky and Sara forgot to wear a dress I was going to be stuck because on Wednesday I would account for ten girls on my own and would never be entitled to change back. Sara then told me she was bored of eyeing up other women and wanted instead for tonight to just be about each other. She wanted to do a new bet. She said, Tonight we will both wear corsets and dress as French Maids. We will then go to the seedy bar and invite the owner to pick one of us to perform and the other will get to film her." "Deal," I said and I knew she looked sexier than me and there was no way the owner would pick me over a woman with a body like Sara's. Both of our outfits were classic black and white maids costumes which had short sleeves but we both wore white cuffs round our wrists. We both wore garter-belts which you could see under our skirts as they were too short to cover the tops of our stockings and our black lace panties were visible if we bent over. So Sara grabbed my hand and we went hand in hand to the seedy bar and asked to speak with the owner and explained our bet. The owner said, "Fine, but you need to both agree to do as I tell you and I want to see the video afterwards to make sure you are not filming any of my other girls or my customers." Then the owner went up on stage and announced, "Gentlemen, tonight we have two French Maids. I am to pick one whilst the other films her. So I pick Paula!" Damn I thought, had Sara fixed this? She could not have done so as she would have had to have been to the pub before. So by a cruel twist of fate instead of watching Sara do a striptease here she was going to watch me do one. So just as I was going on stage to dance the owner told me he knew I was a man so I should under no circumstances remove my bra or panties. The audience filled my bra and panties with money. Then the owner gave me a dressing gown and led me off the stage. He said, "I have a surprise for you. Here's a camera now go and do some filming." I looked out and saw Sara packing up her camera and starting towards the stage to come backstage when the owner announced, Now Gentlemen at no extra expense we have our camera lady maid Sara!" She looked shocked initially but then hid it well and got on stage and ready to begin a routine. I almost felt sorry for her as only one of us was meant to be dancing. Despite losing almost every night I was now to going to get to watch Sara become a stripper. This was why I had agreed to this bet after all. She looked amazing as she took off her maid's costume apart from the cuffs and whilst I was probably the only crossdresser in the crowd I was sure I was not the only person who wanted to sleep with her right now. She started to look like she was really enjoying it as she took off her corset and her fishnets but then for a moment she looked angry as the owner made clear through the music and lighting that she was going to have to take off her bra too as she was not a crossdresser. As Sara had had to remove her bra she had to put all of her tips in her panties which were almost falling off her with all the money stuffed in them. The owner came over and squeezed her ass at the same time palming some of her tips and gave her a dressing gown and showed her back stage. "Paula filmed you as well Sara. Care to see yourself?" he asked. "Look there is no way I can let you two girls go this evening so I have taken your dresses and sent them to a dry cleaners. They'll have them back by tomorrow night. I would like you girls to perform again tomorrow and to sign a contract to do so for the rest of the week. Let me know if you are happy to do so in the morning. I will make it worth your while. I am afraid we are out of food tonight but we have these tablets that the military used to use which act like a whole meal." I took one as I was hungry and the owner asked me to sign a contract. I think I did so and then I watched Sara to do so too. But the contract was limited to the end of the fortnight and as we saw no girls in skirts as we were the only ones wearing that much clothing in the place Sara said that I was now free of the bet.