Date: Sun, 6 Dec 2020 14:23:05 -0700 From: aariel bender Subject: North Cliff Part 14 Philip's Father Harmony North Cliff Part 14 Philip's Father Harmony ~~~~ ~~~~~~~~~~~~ ~~~~~~~~~~~~ ~~~~~~~~~~~~ Please make a monetary contribution to nifty right this minute. Do your part to help keep quality alternative Writing alive and well http://donate.nifty.org/donate.html ~~~~ ~~~~~~~~~~~~ ~~~~~~~~~~~~ ~~~~~~~~~~~~ I was pleasantly surprised to bump into Philip while running errands in town. Philip was with his father, Erin's brother Harmon. Harmon told me he'd heard about me from Erin, and was pleased to meet. As it turned out we were both headed to Ruthie's Lingerie. I was asked to pick up some things Michele had ordered. Harmon Wandsworth seemed a little uncomfortable when we arrived at the shop and he realized I we were both going in. "My two best customers. I see you've met. And little Philip too." The ever cheerful Ruthie greeted us as we entered. "Marilyn has your things in the fitting room. She's expecting you." Harmon excused himself to tend to his business. "I've got Michele's things all ready. Anything for you today?" I told her no, but I'd be back soon when the new styles arrived. "And how about you Philip? I have some things that you'd look very good in. He's a pretty boy don't you think Mr Will?" Philip just sputtered, not knowing what to say. I told him Ruthie was the best and would find him something nice like what I was wearing the other day. His eyes lit up a little. "Oh, so you two know each other intimately?" "Yes, he was at aunt Erin's the other night for a party. He did look good in his pink panties. Maybe, can I see. The ones Erin gave me to wear were silly little girls panties, not nice ones like Will had on" Ruthie took his hand and I followed. This would be exciting watching a boy pick out his first pair of sexy panties. So much for not being a sissy. I doubt she would get him in a dress, but like us other men, he wanted to enjoy the silky pleasure of panties every day. Ruthie put out some things for him too look at. He gently picked up a pair and felt the material. He repeated this six times, for six pairs. While he was choosing, Ruthie went to check on Harmon and then picked out some other things for Philip to consider, slip, babydoll, and tops. I told Philip once he put on a pair he would never want to wear boys pants again. He looked up at me and grinned that devilish grin of his. "So you've met Erin. She's a sweetie and a great addition to our little town. Isn't her shop fantastic? She asked if I knew you. I told her you were someone she should know." I told her now it was Michele's favorite place and that she's been working a little there after school. "Michele loves Erin, her new best friend." "Yes, they are the same sort of free spirits aren't they. I'm glad they've gotten close. So what was this party you went to?" "A little play fun. Philip was my special treat. I think it was to distract me so Erin could spend time with Michele." "Oh my, that sounds fun. A little boy fun for your pleasure. You couldn't have picked a more perfect specimen." Just then the doors to the fitting room opened and a most gorgeous well attired woman appeared, followed by Marilyn. "Oh Harmony, you are stunning. It fits you perfectly." A transformation. I was now looking at a beautiful 35 year old woman. Beautiful face, nice legs, great figure. Mmm, now this father/mother son pair were getting more interesting by the moment. "Mom you look great." Harmony stood in front of me, I could smell her perfume, and asked if I liked what I saw. "Good enough to eat." She laughed and gave me a mock slap for being so rude. Harmony asked Marilyn if she could try on the casual outfit. " "She is very pretty, isn't she Will? Too old for your taste in girly boys?" I told Ruthie I had no problem here. When she returned, Harmony was wearing some tailored pants low shoes and a casual blouse. She made no attempt to inflate her breasts, but she was wearing a bra. Just a cute A Cup figure. The pants were cut to give her nice shapely hips and a small waist. Again we all complimented her. She said she'd take both outfits and would come and try on the other outfits when they arrived. I asked Harmony and Philip is we should take a walk and get some lunch. Harmony wasn't so sure. "I usually only dress at home or with friends. I'm afraid people might stare at me." Philip told her she looked great and he would be happy to go out with her and me. I made it clear if she wanted to live this life, then she should be confident and face the world. Harmony thanked me and gave me a hug. She held me tight, crotch to crotch. I could feel her dick rub against me. I'm sure that was the intention. She blushed a little as she backed away. "You kids go out and have some fun. All your packages will be waiting for you when you return. "Ok Ruthie, wish me luck." I took them to a place I knew we could get a private table to talk and people watch. ======Harmony====== "I'm the oldest of four kids. Erin is the youngest. Our brother and sister are the straight ones in the family. Maybe even a little up tight. I had to hide my cross dressing from them, and my parents. Only Erin knew and would find things for me to wear. My sex life was confusing. I liked women and dated, but I was also curious as they say. I wanted to get fucked like a woman. I got married just out of college. I tried to explain to my wife about these conflicting thoughts be she didn't want to hear it. I dressed up for her a couple of times, but she didn't get it. Then Philip was born and I had to make sure I had a stable job to support us. When Philip turned 8, she packed her bags and left. She's remarried and has no contact with us. I moved down here to work for the Company. Erin followed soon after. I decided to set up my own business. I thought I could change my identity easier that way. I did all my work remote, so no one knew me as Harmon or Harmony. When us Wandsworth kids got our inheritance, it made my life easier and I was able to expand my business. I hired an office manager to be the face of my business. I guess you are the first to meet Harmony Wandsworth. Well, someone who isn't one of my dress up friends." "Philip told me all about Erin's party. She asked me permission to have Philip there. I know he's been with other boys. I'm fine with it and I make sure it's always safe. He told Erin he was tired of boys and wanted to meet a man. She had checked you out and you fit the bill, Will. Philip said he enjoyed the night with you. And he told me the exciting news about his first cum shots, which I understand were not wasted on you. Philip said I might like a date with you. Is this it, or would you invite me out for a special night at your castle?" I gave her hand a comforting squeeze and said I will give her a call for a proper invitation. She just wanted to make it clear, it was a date with just her not with mother and son. She assured me there would be plenty of opportunities for me to have Philip to my own. I called Harmony a few days later and we she agreed to a date. I arranged to pick her up. Her building was only a block away from Erin's. Like Erin, Harmony had bought an old building for her office and living quarters. The ground floor was a snappy old fashion lunch counter that had been restored and was doing a thriving business. Smart siblings finding a secure way to survive in our town. My driver Nettie asked "who is this lovely lady you are taking out tonight Will?" I introduced Harmony. Nettie complimented her on her stylish dress. This made Harmony happy and a little more comfortable. She had the decision to live her life as a woman from here on out. She was nervous but happy to take this important step. Our first stop was the Commons for a drink. This was a service club that raised money to support many causes including LBGTQ issues. My father was on the original board of directors, so when I was sponsored as a member, I was welcomed with open arms. While the club was well known in town, it still operated discreetly. One needed a key card to access the stairs and elevator to the second floor reception. There was no indication at the door or even at reception where this would lead to. I introduced my guest and suggested she may want to become a member. There is usually a formal process to admit new members. My requests were given special attention. The manager came down and escorted us into the office behind the reception desk and took the necessary information. I paid her initial dues and Harmony was issued a key card and sent the information package. The first level of the club was the restaurant and bar. This is what most guest would only see. The second level was the club room. It was a place people could meet, socialize and play cards or board games. There were some booths around the side and private meeting rooms. The third level was the ballroom. The fund raising events included weekly dance nights and the twice a year Big Show. The cloud hired a producer to put on a classic Cotton Club style show with orchestra, singers, dancers, comedians, speciality acts and a lot of fun. Acts were brought in from all over the country to recreate as sort of entertainment from another era. The event had become so popular that there we two three house shows a night, Friday and Saturday. The best tickets were auctioned off. The demand and prestige of a ringside table meant they went for big money, which offset the costs and raised a considerable sum. The other seats weren't cheap and still carried a lot of honor for those who got one. On Sunday there was a young adult matinee. This was supposed to be the G Rated show, with the bawdy and lewd bits removed. That was rarely the case. You still might see an exotic dancer's tits. The club figured kids 16 -20 would be able to handle it. No adults were allowed, so they couldn't complain. The shows were quite the event. Black tie night out. The performers were classic show people. It wasn't uncommon for one of them to appear drunk but the last Saturday seating. The MC would give them the literal hook. It was all in good fun. Even as the boss's son I wasn't allowed to attend the Sunday shows, until I was sixteen but I managed to be around for the rehearsals during the week. I was treated like a mascot by the performers and could roam freely around the coed dressing room. Now that I think about it, this was probably the source of my sexual education and the origin of a couple of my fetishes. The dancers were casual about their state of dress or undress. They all wore period pin up style high waisted panties and bras. I remember picking up a pair to examine a little more closely when the owner came up to me and called me a little panty thief. I remember they were still warm and gave off a delightful aroma. I saw plenty of tits and pussy being put into costumes or even better when they were peeling them off. I must have walked around the a constant boner. The male performers were also an education. I was invited to smoke some of the muggles and have a nip of whiskey. The most memorable moment was when one of the chorus boy dancers called me over to the corner to meet another of the boys. "Frank, show the kid that third leg of yours. It's the biggest piece of meat you will ever see." The guy pulled down his underpants and revealed a monster of a dick. It was uncut which was mysterious to me too. "C'mon Frank, get up up show the boy what you carry around." Frank started stroking it and it grew and grew. The head started emerging from his foreskin like a one eyed snake. The other guy Dan grabbed it and rubbed it too. He said "kid, put your hand here, feel how hard it just got." I gladly tried to wrap my six year old hand around it, with little luck. Dan then told us no reason to let that go to waste and opened his mouth and took it in. His lips moved around it like a fish. I was hypnotized and wondered why he was doing that. He started seriously suck it and jerking it. Frank moaned and Dan swallowed furiously. He licked his lips and said always best right out of the pipe. One of the ladies saw what was going on and scolded them. "You'll turn the boy into a perv." Dan grabbed my crotch and gave it a squeeze. "You like that Will? You should give it a try someday. It's ok and good fun." Now I'm drifting back and getting nostalgic. You really want to know what Harmony and I would get up to. I escorted Harmony to the bar for a cocktail and a chance to settle in together. It was a quiet bar, where conversation was easy. A few members I knew came around to say hello and clearly to check out who the babe I was with might be. Harmony is about two inches shorter than my five foot ten. She had a cute freckled face topped with her medium long blond hair. A pretty smile.She had it nicely styled, nothing complicated. Her face was sculpted and very feminine. Her arms were well toned, not manly looking at all. Best of all were her legs. She really was a knock out. Her voice was soft and had a slightly high pitch. I don't know if this is something she worked at or her natural voice. She chatted confidently with several gentlemen and a couple of the wives with out anyone being anything than friendly. One of my friends said I always seem to show up with the best looking women. After a drink we moved on to dinner. I did want to show off, so I took her to a very special place. Small and very exclusive. If you aren't a regular, there is little chance of getting a table. Harmony asked my why I was single. I told her about Maddy and had decided not to jump back into a long serious relationship. I dated, but wasn't ready for someone else to move in with Michele and I at North Fork. She understood. The talk then turned to our businesses. Harmony listened intently to the story of my success and then new projects. Her business was doing well and she was looking for new clients. After dinner she asked if I wanted to go back to her place for a drink. Philip was with aunt Erin, so we'd be alone. A nice bottle of wine was opened and we had a glass. Harmony was direct. She said she had only had sex as a woman with other crossdressers. She said it was fun, but always felt like it was a game, no romance. Some of the girls were into anal, but Harmony didn't care for that. Just sucking and touching. She asked me if that was ok. I told her I was attracted to her and was agreeable to what ever might happen. With that she stood up and unzipped her dress and let it fall to the floor. She stepped out to show me she was wearing just panties and a bra. She saw me looking and said the bra made her feel good about her flat chest. When she sat back down with me she told me that hormone treatments weren't on her plan just yet. "I have to get comfortable with who I am, before I consider changing in any way. She kissed me. He mouth felt soft and inviting. I let my hands explore her body, with out digging into her panties. I was led to her bedroom. It felt like a woman's space. Soft, but not all pink. Well appointed. There was no hint of a man in this room. "I think you can get undressed if you plan to join me in bed. I undressed slowly, giving myself a chance to take in what was coming next. She did like my panty choice. "Ruthie knows what looks good on you, doesn't she? I think I'm pretty good at sucking a cock. I hope you think I'm at least as good as Philip or my sister. Would you like to find out?" "I would like very much, as long as you let me return the favor. Deal?" With that Harmony began a new phase of her life. Sex as a woman, with a man. She didn't just dive on my dick like a cheerleader. It was a long journey. Our bodies intertwined, trying every possible position. I got on top and rubbed our panties together. I could feel her girl penis grow and make contact with me. I pulled her panties down so I could finally see what she had. It was smaller and thinner than mine. Cut. I pulled my pair down and out cocks made direct contact. She gasped. I wrapped my had around both of our members and stroked them together. "Frotting? That is delightful." I moved to our cock heads and smeared the combined precum on both of us. I knew I had her in my spell now. I went down for the first licks. Her cock fit neatly in my mouth. She was shaved smooth, not a hair on her body. As a blond, I'd doubt she'd have much if she didn't shave. The smooth body enhanced my own pleasure. Once I got Harmony good and hard, we traded places and she was now staring at my hard on. I was a good two inches longer and thicker. She took her time, handling me as if she had a long sought after prize. I liked that. She finally licked me. Harmony looked up, her lightly made up face and eyes. That smile. Then it was time to inhale a man's cock. She went at it like a pro. There was no shyness. Just slow burning lust. I let her get me close to the edge and then told her we would trade places again. Each round, her efforts became more intense, more detailed. She also started talking dirty about both of us. She was a cock sucking sissy whore, I was a faggot fucker. We would continue this oral edging for the next two hours. We took some breaks to make out and to frot some more. "I've never had sex so caring and tender, not even when I was married. Your Michele is a very lucky girl to have you for her teacher and lover. And my son was very lucky to meet you. I can't believe he had this dick before me." Despite Harmony's no anal rule, she managed to get a finger in me. I liked that, she laughed at the bold move. When I couldn't stand it anymore, I went for the prize. It seemed like I was sucking the biggest clit I'd ever known. Despite the dick and balls, it was a woman I was making love to. Harmony was living proof that the size of the organ had no relationship to the size of the load. It was a glorious sweet load I swallowed. I gave her a few extra licks and sucks before I let go. I asked her if she was ready, she answered with her lips. She had a delicate mouth. No hint that she was born a woman in a man's body. I fought hard to not cum too quickly, but the long session had left me so close. When I fired off, her eyes got wide and she struggled to take it all down. She did. Then she looked at me and licked her lips. Mutual satisfaction. The rest of the night was comfortable snuggling and some tender words. Harmony admitted she knew I wasn't going to fall in love with her. I'd help christen her new life. The next day she made me breakfast and we had a talk. This time it was about business. She wanted to take over the management of our new project including the marketing. I told her we thought it would be big businesses who would pay for the security and hacking defense our software would offer. The encryption scheme would make file transfer much safer and defeat hackers before they could penetrate any network. The destructive targeted response would put a lot of bad actors out of business. Harmony leaned over and kissed me and said "let's do business. I think I'd be a better business partner than a lover." Harmony did find a lover. A very nice older gentleman who could appreciate the special sort of love Harmony could offer. Philip was a regular guest at North Cliff. He was nice enough to bring a friend or two around as well. Michele had hoped that Erin and I would become a thing and she would move in with us. Erin was only interested in Michele, and their friendship continued for the rest of their lives. The software project, part one was a huge success. I thought the payout from the first effort was insane, this was that a hundred times over. I sat down with Michele and asked what we should do. She said " let's just stay the same, but can we go on a long vacation, away from here. I want to see the world." I told her to make a plan. It would have to wait until the next summer when we would have two months free. It was agreed. Before then there were more adventures at home.