Sissy Outed Part 4 - Gerald Finds Out free porn video

The story continues from two different points of view. Didi carries on his narrative, but we also hear from Gerald. DIDI: You probably won't be surprised to learn that I haven't worn trousers in the office for a few weeks now. In fact, I spend much of my time in girl mode. The rest of the time (that is, when I'm with Alice) she keeps me aware that I'm not a girl, but that I'm her sissy boyfriend wearing girls' clothes. She often wears trousers when we go out and she likes to look quite boyish to make me even more aware of my sissy status. She insists I always wear stockings and suspenders, never pantyhose (like the others in the office wear most of the time). She knows that I feel much more vulnerable wearing them and that I have to be very careful not to let my stocking-tops show in public. Also, in a cinema - or sometimes even in a restaurant - her roaming fingers can explore up my skirt... She was very pleased to see how I looked on some of the publicity photographs. She had one of the pictures enlarged and framed. It now hangs in the living room. It shows a smiling, attractive, confident office worker in a blouse and skirt. The blouse is business-like rather than sexy, but nevertheless shows the outline of a shapely bosom. The skirt is equally professional-looking, just above the knee and showing an attractive pair of legs. From the picture you cannot tell that she is wearing stockings. Nor that she has a cock tucked into her silky knickers. Over the following weeks I met my sister Audrey several times to make arrangements about the wedding. And of course, to sort out my bridesmaid's dress. I didn't get to decide much for myself, but was measured for it and allowed to choose the exact shade of pink. It came up in conversation that Gerald, the "best man", was a bit of a pain. "It would be really great if the sisterhood got him into a skirt and knickers after the ceremony," said Audrey. (I had already gathered that Helen and Rose had been included in the guest list as a reward for supplying the bridesmaid!) I did get to meet him once before the wedding and had to agree with my sister's opinion. I could almost feel his eyes ogling my bust and legs. Alice was also present, but had chosen to wear a skirt and was not acting as if we were a couple. She wanted to see how he behaved. He tried to indicate (without actually saying so) that the best man would get to have his way with the bridesmaid. "Don't worry," said Alice later. "We have plans for him. But you'll have to play along. You'll have to lead him on a little. Don't worry - girls do this all the time." GERALD: I was really pleased when my best friend from college asked me to be his best man at his wedding. It was the first opportunity I'd had to take a leading role in any more-or-less public engagement. Up to now I'd always been, in family terms (at least), in the shadow of my two elder sisters Mary and Caroline. They didn't have any role in the wedding, although I understood they would be invited. In my honour, of course, as I was to be a key player. I tried to make it clear from the outset that I was very aware of my responsibilities to support the groom. To make sure that he would be at the church on time, that he'd be in a fit state to make his vows; that I would have the rings available at the crucial point in the ceremony; and that I had to make a speech... I was also keen to find out about the bridesmaids. It was going to be an opportunity for me to present myself in elegant formal clothes to one or more young ladies who would be no doubt attired in elegant made-to- measure gowns, but who might well be a little nervous and susceptible to my masculine charms... I found out that there was to be only only one bridesmaid. When I met her for the first time, I was really impressed. She was quite tall with beautiful long legs and well rounded tits. I was almost sure that she wore stockings and not tights, but I never got the chance to see for sure. Didi was a little shy, but didn't seem to be any more nervous about the wedding than (if I admitted it) I was myself. I didn't ever meet her alone, though. There were always one or two other girls with her. DIDI: To go with my bridesmaid's dress, Audrey bought me a pink bra and suspender-belt set, a pink slip, and a pair of gorgeous silky pink knickers, with "Didi" embroidered in red above the left leg-hole. "I never dreamed I'd by buying pretty feminine underwear for my little brother," she laughed. She also gave me a couple of pairs of pale tan seamed stockings. "You need to keep spare stockings with you in case you damage one," she explained. "But be sure you always get your seems straight. I'm sure Alice will help." When I finally got to try on my bridesmaid's dress I was surprised (and a little nervous) to find how short it was. The hemline was only going to be a couple of inches below my stocking tops. The dress flared out below the waist in order to give the impression of feminine hips. "Don't worry darling," said Alice soothingly. "You have lovely legs." There was a little pink hat to go with the dress and a tiny pink leather handbag with a delicate shoulder strap. "You'll need your hands free to carry your bouquet of flowers," she explained. On the big day I was rather nervous as we lined up at the back of the church. Alice held my hand as we waited. Then the organ started playing the Wedding March. My sister glanced back and gave me a big encouraging smile. The procession started off. Audrey looked really special in her wedding dress. I walked a few paces behind, careful not to step on the train of her dress. Heads turned to watch her on the arm of her uncle, who was to "give her away". In her long bridal dress she looked like a queen, gliding along with no legs visible. This made me even more aware of the fact that I was showing so much of my own legs. As I walked past the wedding guests, I was sure I could feel their eyes moving from the bride to watch my bum and my long seamed stockings in my pink shoes with their 3" heels... Although I did share in the joy of the occasion, I was not surprisingly very conscious of my own appearance. There were, of course, a number of family members present who knew that the bridesmaid was in fact the bride's sissy brother. But I was determined to play the part well and ensure that nothing detracted from my sister's special day. The ceremony went very well and then there were the inevitable photographs, which seemed to take forever. GERALD: Mary drove the three of us up for the wedding. We all lived in our mother's house (our father had died some years before). My mother had to stay and look after the family business - apart from her and ourselves there was only one other girl, Christine (not a family member), who worked in the office. It was quite a long journey, so we travelled up the night before and stayed at the hotel where the wedding reception was to be held. On the morning of the big day, I stood at the front of the church with the groom as the organ played the Wedding March. So far so good. The groom was more-or-less sober and I had the rings in my pocket. (I'd checked several times). As the bride arrived alongside the groom, she turned to hand her bouquet to her bridesmaid and I took the opportunity to glance back. I gasped. Didi was dressed all in pink. She had a surprisingly short dress, showing off her lovely long legs. I felt a little tingle in the end of my cock. Would I get the chance to put my arms round her later? To squeeze her, to press her breasts to my body, to touch her legs with my finger-tips (and to find out if she was really wearing sexy stockings...) But then the ceremony started and I had to concentrate on what was going on. The celebrant ensured that everything went smoothly. I didn't drop the rings, and after handing them over, I went to my seat and was able to relax a little and enjoy the ceremony. Everyone applauded the bride and groom before they started the procession back down the aisle. Didi gave me a little smile as we turned to walk down side by side. We didn't touch, of course, as it was a formal occasion, but I was very aware of her presence next to me. She was the same height as me. I could hear her heels as she walked. I didn't look down, but I could envisage her long legs moving under that short skirt. So short that it almost seemed like an invitation to explore what it only just covered... DIDI: While I waited for the photographs to be completed, I couldn't help wondering what "the sisterhood" had planned for the best man. And just how I would be expected to "lead him on a little... " After the meal, the speeches and the toasts, the bride and groom danced in front of the wedding guests. After the music had stopped and the applause died away I saw the best man coming over to speak to me. As if by magic, Alice, Helen and Rose all appeared at the same time. Gerald didn't seem to know what to say, so Alice spoke. "I hope you're not trying to chat up the bridesmaid. He's already spoken for." Gerald stared. "HE???" he asked. "Oh yes," replied Alice, "Didi is my sissy boyfriend. He likes wearing pretty clothes and showing off his lovely legs. They are rather sexy aren't they? Especially in seamed stockings and suspenders." Helen took him by the arm. "Boys are turned on by stockings and suspenders, aren't they? I can tell you are. Wouldn't you like to see more?" Rose took his other arm. Alice put her arm around my waist and we led the way up to Helen's hotel room. I felt Alice's hand caressing my bum as we walked. My cock stiffened. By the time we reached the room I had a throbbing erection. GERALD: After the photos were taken we arrived at the reception. I had to concentrate on what I was going to say in my speech. I was glad when it was over. The music started and the bride and groom had the first dance together. Everyone applauded. I made my way over to where Did was standing. Just as I got there, some other girls appeared. They were all smiling at me. I had never been the object to such concentrated female approval before. Perhaps it was the clothes that made me look so manly, confident, and attractive... Two of the girls took my arms, while the other put her arms around Didi's waist. They introduced themselves as Helen, Rose and Alice. Alice was the one with Didi. I was astonished to hear her tell me that Didi was in fact her BOYfriend! "Wouldn't you like to see more?" asked one of the girls. I allowed myself to be taken up to one of the girl's hotel rooms. Alice and Didi led the way, and as we went up the stairs, Alice was fondling Didi's bottom. I was able to confirm my suspicions that Didi was indeed wearing stockings! And they were stockings with seams and taut shiny stocking-tops. VERY sexy. DIDI: Gerald seemed to be in a trance. His eyes were on the front of my skirt which obviously had something unladylike sticking up underneath. He allowed Helen and Rose to start undressing him. "You'd like to look pretty too, wouldn't you?" murmured Helen. He didn't seem to offer any resistance as the girls gently removed his clothes. Soon he was down to his boxer shorts. Perhaps he though I would be undressing too? Helen put what had been my falsie bra on him. I didn't need it any more, now I had my silicone boobies attached. Rose handed him a pair of silky knickers, peach coloured, with little frills around the leg-holes. He was allowed to turn away to take off his boxers and step into the pretty knickers. He seemed reluctant to turn back round to face us. Helen winked at us as she stood behind him to place a white suspender belt around his waist and the fasten it at the back. She told him to thread the suspenders down inside his knickers. "Now you need to turn round so that we can help you put on your stockings," she said. As he turned rather sheepishly we could see that he had a partial erection. By the time his stockings were attached to his suspenders his cock was rock-hard. Rose took my hand and led me over to him. "Silky knickers always make boys hard, don't they?" she said (I certainly was). She placed my hand on his cock and I held it with my fingers and thumb through the silky knickers. It was the first time I had ever touched another boy's cock. It was firm and warm, but there was just a little give in the flesh. If you've ever sat in the driving seat of an expensive car, you'll know how the control knobs give a little as you grip them, giving you the sensation that they are ready to yield to your command... But in fact I wasn't think so much of driving an expensive car. No, I was reminded of the day I had first met Helen, when she had discovered my newly-bought cock dildo that had been stored in the back of the wardrobe ever since I had linked up with Alice again. And I was reminded how she had made me suck that cock until it spurted into my mouth. I wondered for a few moments whether that was expected of me now... GERALD: We entered the bedroom and Helen and Rose helped me off with my jacket. Although I couldn't actually see Didi's cock, there was obviously something very unladylike sticking up under the front of her skirt. The girls continued to undress me. I could smell their perfume and feel the warmth of their bodies as they brushed against me with their boobs and nyloned legs. Soon I was down to my underpants. I was in a sort of trance. I liked the sensation of having girls undress me and wondered what would happen next. Then one of them held out a bra while the other helped me put my arms through the straps. The bra had filled cups so that it seemed as though I had tits of my own. They spent a little time adjusting the bra-straps until they were satisfied that it was a good fit. "Perhaps you'd like to do the next bit yourself," suggested Helen, handing me a gorgeous pair of silky knickers. They were a delicate shade of peach and had little frills around the leg-holes. I turned my back to the girls while I slipped off my underpants and stepped into the knickers. As the soft cool material slid over my bottom and encased my genitals, I felt my cock stiffen. A suspender-belt was fastened around my waist and I obeyed the instruction to thread the suspenders down inside my knickers. Rose took my arm and I turned back to face them. She supported me as I lifted one leg at a time to allow Helen to put my stockings on. Her face was quite close to the front of my knickers and I couldn't help myself - my cock grew and grew until it was rock-hard, sticking up like a tentpole in my silky knickers. Once all my suspender clasps were fastened to my stocking-tops, Rose let go my arm. She took Didi's hand and placed it on my cock. "Didi - meet Geraldine," she giggled. Didi's fingers gripped my cock through the silky material of my knickers and she held it for a few moments with a dreamy look in her eyes... DIDI Helen came over with a slip and I let go Gerald's cock so that she could put it on him. Next came a red mini-dress with a long back zip and a pair of shoes with 2-inch heels. Then she put a towel around his shoulders while she made up his face. She didn't do much with his hair. It still looked a little boyish. But I realised that they were not trying to make him look like a real girl. Rose, Helen and Alice let him admire himself in the full-length mirror and told him how pretty he looked, then slowly led him towards the door. They were telling him that he would really enjoy himself on the dance floor. Their hands were stroking his body through his clothes, making him aware of his bra-straps and suspenders. They were allowing their tits and thighs to rub against his body. And while he was distracted (and out of sight of the mirror) Helen tucked the back of his skirt into the waist-band of his knickers. "Come on, Geraldine," she said. "Let's dance". GERALD: When I looked at my reflection in the full length mirror, I was quite pleased with the result. I saw a tallish girl in a red dress trimmed with black around the collar. The dress showed off the outline of her shapely bust, and flared out at he waist (although her erection was still apparent). The skirt came to just above the knee. She had pretty legs in black shoes with about 2 inch high heels. She looked (I thought) quite demure and attractive; not a stunner like Didi, but a girl that would not stand out in a crowd. Unless she had an erection, of course. The girls pretended they couldn't see my state of arousal and complimented me on my appearance. "You look really pretty,"said Rose. "Wouldn't you like to come downstairs with us and have a dance? We'll stay with you to look after you." I was a bit apprehensive about the idea, but they slowly led me towards the door. They were running their hands over my body, remarking on my new bust shape, making me aware of my underwear. My bra straps over my shoulders and the back strap. My taut suspenders pulling on my stockings... Eventually I was persuaded, but my apprehension as they opened the bedroom door caused my erection to subside, for which I realised I was grateful. I walked down the stairs very carefully. Although the heels on my shoes were not too high, it was still a different way of walking. It was strange not to be wearing trousers. I did have a belt around my waist, but this was a suspender belt next to my skin, not one to hold my trousers up. My stockings pulled at the suspenders with each step. And they rubbed together with a faint swishing sound as I walked. And I couldn't really feel my skirt, except on the front of my leg sometimes. But the girls stayed with me. "Just be relaxed and confident," said Rose. "There are plenty of young ladies here. You won't be standing out in the crowd." DIDI: As soon as they had left the room, Alice went through the pockets of Gerald's wedding suit to find his hotel room key. She picked up a couple of carrier bags and we went to his room. The suit-carrier from the wedding hire company was in the room and Alice handed it to me along with the key to Helen's room. She told me to go and pack Gerald's suit away. "I'll come and join you in a few minutes," she said. By the time I had packed the wedding suit she came back with the carrier bags, now containing all Gerald's male clothes. She put his money and hotel key in a little black handbag and we went back down to the wedding reception. Geraldine was still dancing with Rose and Helen. No-one had told "her" yet that she was showing her knickers. But there were a lot of smiles around the room. We sat at a table with two other girls, who turned out to be Gerald's sisters. They were very amused at his appearance and were discussing whether to go and tell him he had his skirt in his knickers. Alice gave the hand bag to one of them, saying that his hotel key and cash were inside it. Then she took my hand and led me to the dance floor. When the music stopped, Alice gave me a big hug. "It's been a lovely day and you look wonderful in your bridesmaid's dress," she said. "But wouldn't you prefer to wear a bride's wedding gown for me?" My eyes filled with tears as I accepted her somewhat unconventional proposal of marriage. (That's the end of Didi's story - at least for the time being. But we haven't finished with Gerald yet...) GERALDINE: I danced with Rose and Helen. They kept chatting to me, saying how nice I looked. Everyone was smiling and I smiled too. It was a very happy occasion. I was really enjoying wearing a dress and the novel sensations of feminine underwear - bra and knickers, stockings and suspenders, high- heeled shoes... Suddenly my sisters appeared and Rose and Helen melted away into the crowd. Mary handed me a handbag. "You need to look after this," she said. "Don't leave it lying around. It's got your keys and money in it." "You're looking very pretty,"giggled Caroline, "but you have to be careful when you get dressed, so that you don't get the back of your skirt tucked into your knickers." She smoothed down the back of my skirt and I felt myself blushing with embarrassment. "Don't worry," laughed Mary, "they're very pretty and you've made a lot of people smile. It's probably just as well it was the back of your knickers you were showing and not the front!" We went and sat down and sipped a drink. I suddenly felt rather tired and realised that it was actually quite late. I had been so engrossed in the novelty of being dressed as a girl that I hadn't noticed the time fly by. People were starting to drift away from the dance floor. "I think it's time for bed," said Mary. "We've got a long drive back tomorrow." I had another little sensation of girliness as I searched for my room key in my handbag. Once inside my room I put my bag on the dressing table and, after a bit of a struggle, managed to undo the back zip of my dress. I stepped out of it and folded it neatly over the back of a chair. I couldn't resist looking at myself in the full length mirror. In my underwear and still wearing my heels. Of course, my hand touched my cock through a couple of layers of silky nylon. And a few moments later there were a series of surges through my whole body. It felt as if my balls were emptying as the cum kept pumping out, soaking my knickers and slip. I stepped out of my shoes, feeling quite exhausted. I took off my slip and then my knickers. I wiped my sticky cock with the back of the slip then dropped it onto the floor with my knickers. I then unfastened my bra, and took off my stockings and suspender belt. I stepped into the bathroom and had a quick wash to remove the remaining stickiness. I wiped my face with a paper tissue to remove my make-up and then washed my face. Then I went back into the bedroom. When I lifted the bed-cover I found there was a baby-doll nightie with matching knickers. Without hesitating I put these on and was soon asleep. The next morning I woke and was immediately aware of wearing a nightie and knickers. The memory of the previous evening's adventures came flooding back. I got out of bed and went over to the mirror. The nightie was very short and my knickers were clearly displayed, showing the unmistakable outline of a rapidly growing erection. A few moments later, these knickers were also soaked in cum and lying on the floor alongside the pair from the night before. As I shaved and showered, I thought about what do do with the cum-stained underwear. I realised that I would have to put it into my luggage to take home. I couldn't leave it in the hotel room. I dried myself on the towel and went over to my case to get some clean clothes. I was shocked to discover that there were no male clothes in the case! There were a couple of pairs of knickers, a slip and two packs of tan stockings. I checked all the drawers in the room. There were all empty. There was a pale blue dress in the wardrobe, but no other clothes in the room apart from the red dress and the female items I had taken off last night or this morning, some of which were not in a state to be worn again without washing. Even the formal Best Man attire was missing. Clearly I had no option but to dress as a girl again. I put on my bra and suspender-belt, clean stockings and knickers, the clean slip and the blue dress. Although I liked the red dress, I wanted to avoid the embarrassment of knowing that people in the hotel might remember me wearing it, with my knickers and stocking-tops being displayed at the back. I found a laundry bag in the wardrobe and put the soiled underwear in it, then carefully folded the red dress and put it in my case with the laundry bag. I brushed my hair. Then I picked up my handbag, checked my hotel key was in it, and went down to breakfast. When I entered the breakfast room it was fairly full. Fortunately my sisters were already sitting at a table and there was room for me to sit with them. "Well, Geraldine," said Mary, "did you sleep well?" I nodded. ""We're glad that you decided to wear a frock again and show off your pretty legs," said Caroline. I explained that I had nothing else to wear; all my male clothes had disappeared. Caroline laughed. "Girls are always saying they have nothing to wear. We'll have to see if we can help you out!" I had a light breakfast. I felt quite girly sitting at the table eating fruit salad and remembering to keep my knees together. Then we each went up to our rooms to pack our cases. As I climbed the stairs I could hear someone walking along the landing below. I wondered if they could see up my skirt.. It didn't take me long to pack. After all I didn't have much to put in the case!. I carefully folded the red dress and put all the cum-stained underwear into a plastic laundry bag. The only other clothes were spare knickers and stockings. I collected my hairbrush and other things from the bathroom and that was it. I quickly glanced round the room to make sure i hadn't left anything, then picked up my case and my handbag and went down to reception. I waited a couple of minutes until my sisters arrived. We handed the keys to the young lady at the reception desk. "Checking out?" she asked (as they always do). She checked the numbers on the keys with the reservations on the computer screen. "I have a Miss Edwards and a Miss Edwards and a Mr Edwards," she said with a querying tone. "That's right," said Caroline. "MISTER Edwards will pay for all of us," indicating with her hand that I was the one who would be paying. The receptionist gave me a broad smile and I handed over my credit card. I put the hotel receipt and my credit card into my handbag and we were about to leave when the receptionist called out, "Oh, MISTER Edwards." I turned back towards her. She was smiling and I noticed that another couple waiting to check out were looking at me in some surprise. "This bag was left for you to pick up. I think its your hired formal outfit." I murmured my thanks. "No problem MISTER Edwards," she said. "Have a nice day!" As we walked out of the front door I could hear voices at the reception desk talking and laughing. "Don't worry," said Caroline. "You're a long way from home. You'll never see these people again." "The main point is," said Mary, "They didn't know you were a mister until the word was used!" We put the cases in the boot of the car and Caroline held the back door open as I got in. "It takes practice to get in and out of a car without flashing your knickers," she laughed. Mary started driving. I still felt tired from the adventures of the day before and soon drifted off to sleep. I woke up when the car stopped. I didn't know where we were. We had parked in a large car park where there were already many cars. Looking round I realised we had come to a large out-of-town shopping mall. As we walked towards the shops Caroline said quietly, "Remember. Boys like looking at girls, at their boobs and legs. Don't look at them or make eye contact. And never look back when a boy goes past." We went into a beauty salon. We were very fortunate that it was possible to be attended to immediately without a reservation. My sisters explained that "Geraldine wants to look a lot more girly and needs a make-over." They didn't actually say that I was a boy, but I think the hairdresser understood perfectly well. Mary stayed in the parlour with me while Caroline went off to look round the shops. Over the next hour or so my hair was styled, my ears pierced, my nails manicured, my eyebrows plucked and trimmed, and cosmetic skilfully applied. By the time all this had been done, Caroline had returned. We left the beauty parlour and Caroline led us to the stores she had visited and showed us dresses, skirts and tops, etc that she thought I might like. Eventually we got back to the car laden with our purchases: clothes, underwear, shoes, lipstick, perfume... Finally we got home and I followed my sisters to the front door, somewhat nervously. My mother seemed rather surprised at my appearance, but managed a smile. "Doesn't Geraldine look pretty, Mummy," said Mary. "He met another boy at the wedding who was wearing a dress and it made a big impression on him!" "Yes," chimed in Caroline, "and remember how we used to dress him in girly things when he was little. You told us to stop in case he started to like it. But this wasn't our idea. We just helped a little after he'd taken the plunge." "Well you're old enough now, er... Geraldine, to decide how you want to dress," said my mother, "but a few explanations will be needed to some people. Like Christine in the office, for example." So on the next working day, my sisters led me over to Christine's desk and explained that Geraldine had decided to change his appearance and would be wearing skirts and dresses from now on. Christine gave me a curious smile and said that I looked very feminine. I felt myself blushing a little. She hadn't really smiled at me before. I had got the impression she wasn't interested in boys and only she had only previously spoken to me in an efficient professional manner. And only when necessary. Over the next days and weeks our relationship blossomed. I was now answering the phone to customers as Gerry (she answered as Chris). She would now come over to my desk to ask me things, and her hand would gently touch my shoulder or back, reminding me (or maybe both of us) of the presence of my bra straps. It wasn't long before she invited me round to her place one evening. She provided a lovely meal and I had taken a good bottle of wine. After eating we sat on her sofa and she put her arm around my shoulders. "You know, you used to be a bit of an inconsiderate male," she said. "I like you much better as a sissy." She kissed me gently on the cheek and put her hand on my knee. I submissively allowed my legs to part and her fingers started to explore up my skirt as she kissed me again. I felt a shiver of delight run up my spine as she caressed the bare flesh above my stocking tops. My cock stood to attention. Moments later she grasped my erection, and at the same time her tongue pushed into my mouth. I had the strange sensation that the cock she was fondling was pushing itself into my mouth... I soon found myself lying on the hearthrug with my dress above my waist and my knickers around my knees. Her warm juicy cunt was pleasuring itself riding my cock. She was in control, keeping me on the edge of orgasm. And when at last my body jerked, emptying my balls inside her, her cunt muscles tightened their grip, milking the last drops until my shrivelled dick escaped from inside her. She stood up. "Come on Gerry, I don't wasn't to make a mess," she said, indicating that juices were starting to ooze out of her cunt. I pulled up my knickers and knelt in front of her. My tongue collecting the escaping juices, hers and mine combined. Her hands gently but firmly held my head in position until she was satisfied. "Thank you, Gerry darling," she murmured. "I enjoyed fucking you. There's just one thing though... you need to remove all your pubic hair. Remember all those Sissy S-words: Silks and Satins, Soft and Smooth, Stockings and Suspenders." [Later I discovered another pair of Sissy S-words - Suck and Swallow - but that's another story.]