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Friends with Benefits By Teri Franken Chapter 1 My daughter was grown up and away at school, the dog had died and my wife was ready to do her own thing. I found myself divorced and on my own in Chicago, just my job and my "hobby" to keep me company. I was an upper level manager at an electronics company and made a nice six figure salary. As for my hobby, well let me say that I enjoy being comfortable when I am at home, and when I am dressed in women's clothing. Yes, I am a transvestite or cross dresser, without any desire to change my sex or to go out in public and be accepted as a woman. I just like to dress up when I am home by myself. My ex-wife knew of my hobby and while she was not enamored of it, she did put up with it, as long as she did not have to see me when I was dressed. Needless to say, I did not dress often during our 17 years of marriage, only occasionally on a business trip in the comfort and safety of my hotel room. Once the divorce was final and I had moved into my new condo, I decided to dress up whenever I was home and to live my life the way that I wanted, without fear of what anyone else thought. Most nights I would come home from work, open a bottle of beer and head to my bedroom to change out of my drab male attire into something I felt much more relaxed in wearing. Tonight would be no different, as I took off my shirt and tie which revealed the satin and lace camisole I had been wearing. Next came the trousers and the rest of my sexy underwear was revealed in the full length mirror of my closet! I had started "under dressing" for work ever since the divorce. Maybe an explanation of the term under dressing is required? Each day, under my business attire, which was very masculine on the outside, I "under dressed" in beautiful feminine finery which was invisible to everyone, but it made me feel so sexy and nice during the day. At a minimum, panties, pantyhose, camisole and sometimes stocking and garters when I felt really daring. I had tried to wear a bra, but was very concerned that it would be visible under my shirt and did not want to make a spectacle of myself. I would normally come home and add the matching bra to the lingerie I was already wearing. I would also insert the breast forms to complete the image I wanted to project. My favorite black pumps with the three inch heel, black satin blouse and white faux leather skirt completed my outfit. I sat at my vanity and added some clip on ear rings, a touch of lipstick, mascara and eye shadow and a spritz of perfume. I pulled on a wig cap and then chose my black page boy wig as the crowning glory. I smiled at myself in the mirror, knowing that I look like a guy in women's clothing, but that is fine with me! My body size and facial features would never let me pass as a woman and I have no problem with that at all. I am over 6 foot tall without heels, weigh 215 pounds, and have short brown hair. After I get done dressing, I make myself a nice meal, read the news paper and snail mail before I go online to live out some fantasies. After dinner, I went back to my bedroom, removed my outfit and put on a royal blue baby doll night gown with matching string bikini panties, removed my makeup and wig and then headed into my spare bedroom which was set up as a home office. My office was more for pleasure than work really, I had my computer on the desk and the monitor was a 52 inch wall mounted plasma television! I had a camera mounted to the top of the screen with a remote control which allowed me to zoom, and basically control the camera from my desk. I sat down and logged into my personal email and checked for new messages. I was anxious to see if I had anything new from my friend Michelle, we had been exchanging notes off and on over the past few weeks and we had really gotten to know each other well. I sensed something different about her, we seemed to have a lot in common, from our dressing habits, our outlook on life, sports and even had comparable jobs. She lived in the suburbs, but commuted daily downtown on the commuter train. In our last e-mail exchange, Michelle had said that she was going to get a camera for her PC so we might chat in real time! Michelle was very much like me, a guy who enjoyed being feminine and dressing in women's clothing, but she also had no designs on ever going out in public and she also considered herself a man in women's clothing. A girl after my heart! She was a widower and was getting lonely at night. We met through an on line CD website and started exchanging e- mail on a regular basis. Michelle had posted a picture of her from the neck down wearing a black satin nightgown and her self description mentioned that she considered herself bisexual, versatile and she was looking for a kindred spirit, a friend with benefits. We are both in our early forties and have similar body shapes, both of us enjoyed under dressing each day. Michelle has short black hair whereas I have brown. There was new message from Michelle mixed in with other messages from other girlfriends and admirers. I quickly opened Michelle's message and a smile came to my face and a stirring in my panties to go along with it. "Hi Teri, I won't be on line tonight since I am on my way to pick up a cam! I have some other errands to run too so I will wait until tomorrow night (Friday) to be on line at 7. I'm looking forward to "seeing you" so we can finally talk to each other real time. I am so excited and plan on wearing my sexiest outfit for ya! Hugs, Michelle XOXO" Wow! This was too good to be true and my cock was throbbing in my panties as I read and re-read Michelle's note. We were finally going to see each other on camera in a private, one on one meeting and she was going to dress sexy for me too? I responded back to her that I was anxious to chat and that I would dress sexy for her too. I closed down e-mail and logged on to the cross dresser dating site to see who else was online. The site had an excellent chat room that allowed you to use your cam when you wanted to or just be on line to chat in the regular text mode. If your camera was not hooked up, you could still see what others were doing on their camera and just chat. It also had the option of going into a private chat so it was perfect for what Michelle and I needed. I chatted with some friends for a while before finally logging off for the night. I went back to my bedroom and washed up, lubed my ass in preparation for some toy play and then moved back to my king sized bed. I turned on a she male video, opened my bedside drawer and removed my favorite dildo and lay back on the satin sheets, never taking my eyes off the large screen television mounted on the wall above the dresser. For the next hour I watched the video while working the dildo in and out of my ass until I had a satisfying orgasm from the ass play, without ever touching my own cock! The whole time I was pleasuring myself I was thinking of Michelle and how I wished it was her plowing me instead of my dildo. I shut off the video and fell asleep with the dildo in my ass and Michelle on my mind..... The alarm went off at the usual time and I awoke with the sticky sheets stuck to my side and the dildo lying in a pool of cum, it must have slipped out at some point during the evening, but I had slept right through it. I got up, grabbed the dildo and brought it with me to clean both it and myself up for the day. I slipped out of my nightgown and put it into the special hamper for my lingerie and then stepped into the shower. I took a nice long shower, shaved the stubble from both my face and legs and underarms, and then got out to pat myself dry. As I stood and brushed my teeth, I looked at the reflection staring back at me and thought that I looked pretty good for my age, I had no discernable body hair, just a heart shaped patch around my pubic area, not quite a feminine shape, but still looked good. I hoped that Michelle would think the same. As I continued to brush, my mind wandered to what would happen tonight. I wanted it to be special for both Michelle and I, so I carefully considered what I would wear. I made up my mind and also decided that I would come home early to prepare for the meeting. I moved to my closet and chose my lingerie for the day, it was to be all black, my very favorite. I slipped on the black satin camisole, black garter belt, black fully fashioned stockings, and a black g string panty completed my "under dressing". I reached for a black dress shirt, gray pants, and a black belt and then stepped into my favorite black loafers to complete my work attire. I grabbed my gray wool sport coat and headed out to the kitchen for a quick cup of coffee before I left for work. I could barely function at work, between the feel of the sexy undergarments and knowing that I was going to chat with Michelle, I was very distracted all day. At around two, I told my personal assistant that I was going home for the day and left the office. I grabbed a cab and got back to my place by three. As I was unlocking my door, my cell phone began to ring, and from the ring tone, I knew it was my ex- wife. I was hoping that she was not going to ruin my planned evening, but it wound up being a civilized call, she let me know she was on her way to Phoenix and would let me know her new address once she was settled. She decided to move to Phoenix so she could be near our daughter and away from me! Our old house was sold and she was severing her ties from the Chicago area, which was a relief for me, but sad in a way too. I wished her well and told her to have a safe trip and to give our daughter Susan a hug for me when she saw her. I hung up the phone and felt a twinge of sadness but then decided it was for the best and it was time for both of us to move on with our lives. 'It is time for Teri to open a new chapter in her life' I thought as I went to the bedroom to get out of my masculine attire. As I was changing I looked around the room and realized how much I loved my condo; it was one of the few highlights of the past couple of months since the divorce. It was located in the northern Chicago, Lincoln Park area and was very convenient to all of the amenities that city living has to offer. It had two bedrooms (one of which I used as an office), a living room, den, dining room and kitchen, also a small laundry area. The view from the balcony overlooked Lincoln Park and the city skyline. I had a garage with security where I parked my car, but mostly used public transportation to get around the city. Now I just needed a friend with benefits, like Michelle identified in her description on her personal page. I hoped that she and I would be able to become just that! Chapter 2 I knew exactly what I wanted to wear for the video chat, so I removed my outer clothing and hung them up in my closet on the male side and then turned to Teri's side to get what I needed. I moved back out to the bedroom, lay the outfit on the bed and then slipped out of my lingerie so I could shower again and begin getting ready. I gave myself an enema before I showered, and then inserted a lubricated tampon in my ass. I checked my face for stubble and decided to quickly re-shave even though there was not much there, but I did not want to spoil the effect for Michelle. Back to the bedroom and digging around in the dresser I came up with the lingerie that I wanted, everything in black, demi cup bra in satin and lace, matching panties and garter belt, fully fashioned stockings and a satin slip that was just the right length to go with my outfit. I put on the garter belt first, then the stockings, then slid the panties on over the stockings. I stepped into my black pumps and turned to look at my reflection in the full length mirror, and liked what I saw staring back at me. I felt a stirring in my cock, but did not take any action, as I wanted to save myself for Michelle later on. I went back to the dresser and put on the matching bra and inserted my breast forms, and then I pulled on the slip, enjoying the sensual feeling as it slid into place and came to a few inches above my knees. Moving back to the bed, I slowly picked up the LBD (little black dress) that was the final article of clothing. I stepped into the dress and pulled it up to my hips, then put my arms in the sleeves, enjoying the feel of the sexy dress. I reached behind and pulled the zipper to the top and then turned to admire my reflection once again. The dress had a fitted bodice and flared bottom that swayed with each turn I made. I loved the look and hoped that Michelle would also. Next came the wig cap as I sat down at the vanity to apply my makeup. I wanted to look extra nice for Michelle, but did not want to over do it. I carefully applied the mascara and eye liner, added a bit of foundation and a dusting of rouge, outlined and then filled my lips with a cranberry colored lipstick. Pearl clip on earrings, along with a single string of pearls necklace completed the jewelry, then a spray of perfume. I stared at my selection of wigs and finally decided on the shoulder length black one, which really offset the dress nicely. I did some light touch up on the wig and checked myself once again in the mirror, liked what I saw and headed out to the kitchen. I still had over an hour before I was supposed to hook up with Michelle, so I opened a bottle of wine and sat down to sort through my mail and to look at the advertisements from the newspaper, hoping there would be a sale this weekend, I loved shopping on Michigan Avenue on the weekend. There was nothing of interest in the mail, and the sales were not very interesting either, so I decided to go ahead and see if Michelle was on line. I refilled my wine glass and headed into the office and fired up my PC. I checked my e-mail first and answered a couple of messages from my friends. I had found a few friends on line, but found that most admirers were not reliable. They mostly wanted a picture or some hot chat to get off on and then they left you hanging. I did not think that Michelle would be like that, but the thought was in the back of my mind as I logged on to the CD site. Michelle was not on line yet so I just checked the new personals to see if there were any new girls or admirers from the Chicago area. At exactly seven, I received a message from the system letting me know that Michelle was on line and almost immediately received a chat request from her! We connected in the text mode, and then agreed to go private in text mode. We exchanged pleasantries and then agreed to go to cam mode; my hand was shaking as I hit the icon to activate my camera. I was set up for split screen mode so I could see both of us and anxiously waited for Michelle to appear next to me on the big screen. There was a slight delay and then, there she was! We both just sat and stared at each other, without saying anything, but with big smiles on each others face. "Michelle, can you hear me?" I asked tentatively. She answered back that she definitely could hear me and that she liked what she was seeing. Michelle was dressed in a beautiful red sheath dress, and the camera was set up at an angle so I could see her whole profile and I could tell that she was sitting in her home office too. "My god, you are beautiful" I gushed and I was immediately rewarded with a big smile and the cutest blush you could imagine. "Thanks Teri and I have to say the same to you, and that dress is to die for!" And we both giggled and the ice was broken, and we could both tell this was going to be a special friendship. We chatted for almost three hours, showed each other our favorite outfits, talked about shopping, football, golf, lingerie, makeup, dress sizes (we were the same!), sex toys and anything else that came to mind. We shared our secret wants and desires, including what we liked and did not like in a sexual relationship. Michelle told me about how she was a widow(er) and how she had a son and her decision to live her evenings as Michelle, but her days as Mike. She was very comfortable in her own skin, happy to have both Mike and Michelle as part of her life and she did not care what anyone else thought about that. "Teri, how about you and I meet for a drink tomorrow? I can take the train downtown and we can get to know each other in person, only it would be as Terry and Mike? ". I quickly agreed and we decided to meet at the ESPN Zone just off of Michigan Avenue at two the next day. We could get to know each other better, watch some College Football and have a few drinks. "Before we log off, how about we both change into our nightgowns?" I said with a smile. She agreed and told me to go first because she wanted to see me stand up and walk again; she said it with a wink and a smile. So I stood up and seductively walked out of the office to change in my bedroom. I carefully removed my wig and cap first, then came the dress and lingerie and jewelry. I chose a cute baby doll in black satin with a fitted bodice that helped to accentuate my breast area, almost giving me a hint of cleavage. I put on my black marabou slippers, redid my lipstick and headed back to say goodnight to Michelle. Michelle was still not back, so I made sure my camera was adjusted to the best angel so she could see my heels as well as my nightgown. Michelle came into view and my heart skipped a beat as I took in her new outfit. She was dressed in a beautiful blue satin short nightgown and I groaned my approval to her. "Teri baby, stand up and let me get a look at you, please?" and she did not have to ask twice, as I stood and did a little twirl. "I guess you like what you see and as you can tell I like what I see" she said as she stood up and lifted the hem of her nightgown. We both had bulges in our panties! We both agreed that this was a special kickoff to our new friendship, we felt very comfortable with each other. Even with our wigs off, we were still turning each other on, and that was a good sign, right? "I will see you tomorrow Teri, please think of me when you are sleeping and be assured, I will be dreaming of you too" she said as we both logged off for the night. Chapter 3 I woke on Saturday morning with my dildo still in my ass, a hard on in my panties and a smile on my face, this was sure to be a special day! I gently removed the dildo from my ass, got out of bed and headed to the bathroom to get cleaned up. After my shower, all over shave, feminine douche and tampon insertion, I slipped into a silk dressing robe and went to relax with my morning coffee and the newspaper. I found it hard to concentrate on the news; my mind was racing in excitement over meeting Michelle in person that afternoon. I spent the majority of the morning cleaning up the condo, doing some laundry and I changed the sheets on my bed. I was hoping that if Michelle and I hit it off in person, maybe she would agree to come back to my place afterwards. Around twelve thirty, I decided to go ahead and get dressed, so I headed back into the bedroom to decide what to wear. My outerwear would be easiest, blue jeans, button down dress shirt covered by a v neck sweater and a comfy pair of sneakers. I stared into my lingerie drawer for at least 10 minutes before deciding on the right things to wear. I finally decided on a complete set of baby blue nylon and lace lingerie. I had recently ordered them from an online boutique and this was the special occasion that called for them. I attached the garter belt around my waist and then stepped into the matching slinky panties, pushing my cock down between my legs before it had time to get any harder. I could feel the string from the tampon hanging from my ass; it felt kinky and naughty at the same time. I moved over to the vanity and sat down to put on the fully fashioned stockings, attached them to the garter tabs and stood up to look in the mirror and contemplated whether to put on the bra or not. I finally decided against the bra and slipped on the matching camisole top to complete my under dressing. I pulled on my jeans, shirt and sweater and sat down to tie my sneakers when I noticed the stockings below the pant leg and decided I had better wear some ankle socks too! Once I had my sneakers on, I was ready to head out to meet Mike, and I was very excited! I hailed a cab for the short ride over to ESPN and enjoyed the beautiful fall day in Chicago. I paid the cab driver and headed into the sports bar, hoping I would be able to recognize Mike in his male drab attire, but was soon put at ease when I heard him call my name. I turned to see him approaching me with a big smile and his hand stuck out, which I quickly and firmly gave a shake. We grabbed a booth and it was amazing how quickly we were both at ease with each other. We drank a few beers, exchanged jokes, watched some football and got to know each other better. As the beer started to take effect, we got more comfortable talking about our lives and lifestyles. Mike mentioned that he really liked my outfits from last night and I of course told him how much I enjoyed his too. He asked if I was under dressed today and after I explained what I was wearing, he winked at me and asked if I would meet him in the rest room in a couple of minutes! I did not hesitate to nod my head and he stood up and went ahead of me. Since it was so early in the afternoon, there were not many people in the place as I made my way to the men's room. As I entered the bathroom, I noticed that there were three stalls and the dividers went all the way to the floor...how convenient! I moved over towards the stalls and found only one had the door closed, so I gave a tentative knock and whispered Mike's name. The door slowly opened and I heard him say to come on in, so I stepped inside and found Mike with his pants down around his ankles. I gasped when I saw that Mike was wearing black satin panties, garter belt, stockings and he had unbuttoned his shirt to reveal the matching bra! He asked me to show him my lingerie too and he also let out a gasp when he saw mine. We both stood there admiring each other and our cocks were beginning to strain the material of our panties. I reached out to rub the outline of his cock through the satin panties as he reached up to pull me closer. Our lips met and we gently kissed as we rubbed each others erection through the panties. "Mike, would you like to come to my place? We could get much more comfortable there and not have to worry about anyone walking in on us." I said with a slight moan. He looked me in the eyes and I could tell that he was ready to follow me anywhere! We quickly composed ourselves and I left the stall first. "I'll meet you out at the table" I called out as I left the bathroom with a big grin on my face and a hard on in my panties. I called the waitress and closed out the tab as Mike approached the booth. Mike grabbed his beer and chugged it down and to everyone that was near us, we were just two buddies out on a Saturday afternoon having a few beers, and that was exactly how we wanted to portray ourselves when in public. "Let's get out of here, we can go watch the end of the game at my place" I said to Mike as the waitress gave me my credit card receipt. As we walked down the stairs, I could feel Mike massaging my ass, and I liked it! We chatted like two buddies as we rode the cab to my place. Mike paid the fare and we took the elevator upstairs to my condo. "Come on in and I will give you the quick tour" I said as I closed the door behind us. Apparently Mike was not ready for a tour as he took me by the arm, spun me around and began to kiss me hungrily! "Oh Teri, I have been waiting for this moment and want you so bad" he breathed into my ear as he worked on unbuckling my belt. "Me too" I said as I started working on getting her pants off too. I took her by the hand and pulled her towards the bedroom where we both took off the remainder of our male drab clothes. Michelle came to me and knelt down in front of me, rubbed my cock softly and then gently pulled it from my panties and took it into her mouth! As she sucked and deep throated my cock, she was rubbing my ass and hesitated for a moment when she found the string to the tampon dangling from it. "Oh Teri, you are such a hottie, I can't wait to plug your ass with my cock" she whispered before she took my cock back into her mouth. I softly moaned my approval and reached down to play with her nipples through the soft nylon cups of her bra. She quickly picked up her pace and as I was approaching the point of no return, she pulled the string on the tampon as I climaxed and nearly collapsed to the floor! Michelle stood up and sensually licked her lips before she kissed me deeply while gently pushing me back towards the bed. I stepped out of my panties as Michelle laid me on my back on the satin comforter and then lifted my legs to put my ankles on her shoulders. I knew what was coming and I was more than ready as she leaned down to kiss me and I guided her cock to my pre-lubricated ass. This was a first for me and I loved it! I had been using my dildo for a long time, but feeling the heat of Michelle's cock in my ass caused me to moan out loud. "Oh my god! Please don't stop, this feels amazing" I cried out much to Michelle's delight. Much to my amazement, I was as hard as a rock again and I reached down and started to play with my cock with one hand and my nipple with the other as Michelle continued to pound my ass. I turned my head to the side and was rewarded with the reflection of us in the mirror and then felt Michelle tense up and finally shoot her load deep into my ass. She reached up and gently removed my ankles from her shoulders and slipped out from my ass, then sat down on the bed beside me. "Teri that was the most amazing sex I have ever had! I did not know it could be that enjoyable, and I can tell that you enjoyed it too. I think I have found that friend with benefits I have been looking for in you. I hope you feel the same way" she said with a questioning look in her eyes. "I couldn't agree more!" I said as I took her into my arms and smothered her with kisses. "Will you please spend the night?" I begged her with a little pout. "I thought you would never ask!' she said excitedly. We agreed that we need to get cleaned up a bit, so we took off our now well stained lingerie and took a shower together. Michelle playfully dropped the soap and I took the liberty of fucking her right there in the shower which I followed up with a blow job that made her head spin. After the shower we dried off and headed back into the bedroom, to find something to wear. I showed Michelle all of the choices and she decided on a nightgown in chiffon yellow satin and we searched and found a pair of panties that went well with it. I chose a similar nightgown in a light pink along with pink panties. I took her hand and showed her around the condo, when she saw the laundry area, she asked if she could wash her lingerie, so it would be ready for the morning. I showed her how to set the gentle cycle and we put on a load of lingerie, knowing there would be even more soiled lingerie after the night was over. We opened a bottle of wine and sat on the couch and talked about what had happened today and what the future may hold for our friendship. We cuddled on the couch and watched some college football, but I could not tell you the names of the teams who played, we were too busy hugging and rubbing each other! At about 10, I stood up and took Michelle's hand and said "let's get even more comfortable" as I pulled her towards the bedroom. With stiff cocks tenting our panties and nightgowns, we slipped under the satin sheets. We spooned together and fell into a happy and deep sleep. Chapter 4 I slipped out of bed quietly at the crack of dawn and sneaked into the kitchen to put on some coffee, then tip toed to the bathroom to get cleaned up. I wanted to surprise Michelle with breakfast in bed and an eye opener of a blow job to start her day. After my shower, I quietly entered my closet, slipped on some fresh lingerie, all in black, but I left the panties off. Garter belt, stockings, bra with breast forms went on first, and then I slipped on my black pumps. I reached up and took my favorite outfit down, and slipped into my French Maid outfit with the fluffy petticoat and turned to look in the closet mirror and was pleased with what I saw. My hard on was hidden beneath the folds of the petticoat. I eased the door open and checked on Michelle, she was still sleeping soundly as I sat at the vanity to put on my wig and some basic makeup. In the kitchen, I filled a carafe with coffee and placed it on a tray with two mugs and two containers of yogurt, added a vase with a flower and headed back into the bedroom to give a friendly wake up to Michelle. I set the tray down and cracked the blinds to let the sun fill the room, then moved over to gently pull the covers back from sleeping beauty. She looked so cute laying there in her yellow satin nightgown; I gently pulled at her panties and worked them down her legs to expose her semi rigid cock in all its glory. I leaned over and took her cock into my mouth and gently began to lick and suck until I felt it harden and then felt her hands on my head, encouraging my actions! I turned my head to the right, never losing contact with the object of my affection, and looked into the smiling eyes of Michelle. "Oh Teri, this is what I call a wake up! " she said as she reached out to feel under my petticoat, only to find I was not wearing panties and was leaking pre-cum already! Michelle scooted over to the middle of the bed, as I tried not to let her cock slip from my eager mouth. I climbed up to join her on the bed and she grabbed me by the hips and encouraged me to straddle her and she guided her cock into my ass. "Does my maid enjoy that?" she asked as she began to pump into my ass while playing with my cock under the fluffy folds of my petticoat. "Oui Oui Madame" I sighed as I leaned forward and kissed her deeply. I felt Michelle start to stiffen up just as I shot my load all over her sexy nightgown, then felt her shoot a warm load of cum deep into my ass. "Wow Teri, what a nice way to wake up. I would like that to happen every day, maybe I could return the favor one of these days" she said with a smile as we sipped our first cups of coffee. "Can you take a day off tomorrow" she asked with a mischievous grin? "How about you come out to my place, we can play some golf this afternoon and you could spend the night with me. Please say you will" she pleaded. How could I say no to the best friend I ever had? I quickly nodded my approval and pulled her up and towards the shower, we had some sticky stuff to clean off our bodies. After the shower, I dressed in a pair of casual pants and a golf shirt with a windbreaker; of course I had panties and pantyhose underneath. Michelle grabbed her clean lingerie from the dryer and got dressed too. I packed an overnight bag, some lingerie, my shaving gear and some clothes to wear on the trip back. I grabbed my golf clubs and we headed down to the garage, got in my car and headed out to the 'burbs' for a continuation of a beautiful weekend. I mentioned how amazing it was that we could so easily do guy stuff with each other and then do girly stuff too. Michelle agreed that we had the best of both worlds going on and she could not have been any happier. She lived in a smaller town about 15 miles west of the city, and it took about forty minutes to get there. . She lived in a ranch style patio home that was on a golf course in a town called Crystal Lake. "You forgot to mention that you lived on a golf course!" I said as we entered the Boulder Ridge golf community. We stopped at her place so she could put on some fresh clothes and get her golf clubs too. Mike was a member of the private club, so we did not need a tee time and the view of the course from his home was amazing. His house was located along a fairway (fifth as I was later to find out) and had a deck that overlooked the course. I stood out on his deck daydreaming as he changed clothes. "I will show you around when we get back" he yelled and motioned for me to follow him to a doorway off the kitchen. It opened into the garage and there was a golf cart sitting there, plugged into the wall. "Why don't you grab your bag, and let's go play, then we can have some lunch before we come back" he said and I nodded my head in agreement. It was a great round of golf, Mike was a very good player and we made a five dollar bet on the outcome, unfortunately for me, I lost by three strokes. After the round, we had lunch in the clubhouse and I was amazed that everyone seemed to know Mike and they all came over to our table to say hello. Mike winked at me and said "I wonder what they would think about Michelle" and then he started laughing and I joined right in with him. We had a few beers with lunch, watched a bit of the NFL on television and then decided it was time to head back to his place. We joked about what it would feel like to wear one of the sexy outfits that some of the women professionals wear in the LPGA as we drove back to his house. We both agreed that is was hard enough to concentrate on our game while wearing lingerie under our clothes without the addition of sexy short skirts. We would never be able to finish a hole without shooting a load in our panties! What a sight we would make. We both agreed that we were best off developing our new relationship as girlfriends behind closed doors, a secret only he and I would share with each other. After we parked the golf cart in the garage, I grabbed my overnight bag and followed Mike back into the house. Once the door was shut, he took me by the hand and brought me on the grand tour of the kitchen, dining room, living room with fireplace, we walked down the hall and he opened the first door. "This is my home office, I like to be comfortable when I work" he said as I took in the room. The room was set up perfectly, book cases, oak desk, and computer with a large monitor. He showed me how the computer was set up to be able to use two monitors, the one on the desk as well as the plasma flat screen on the wall. I was even more impressed when he showed me that all of the components were wireless so he could control everything from anywhere in the room. There was also an overstuffed lounge chair with a reading lamp at one corner. The next room was a spare bedroom that was decorated with slightly masculine tones, a king sized bed, dresser and he explained that the room was set up for when his son came to visit and brought his boyfriend with him. I looked at Mike with surprise and we sat on the bed and he told me more about his family situation. He had married an older woman named Susan when he was 20 years old and she was in her early forties. She knew all about Michelle and they spent many wonderful years together, until she passed away a few years ago. I reached over and gave him a hug when I saw his eyes starting to well up. "Thanks Teri, she was a wonderful woman, nonjudgmental, caring and the best friend I could have ever dreamed of having in my life. Our son Thomas is the most important thing in the world to me; he is openly gay and lives in Chicago with his partner, he knows all about Michelle and is fine with it. Tom's partner is a rather effeminate sissy while Tom is very macho in their relationship" he said with a smile. I told Mike that I would very much like to meet Tom and Steven/Stephanie and he excitedly gave me another hug before taking my hand and pulling me out of the bedroom into the hallway. "Come on, let me show you the rest of the house" he said. There was a full bath in the main hallway and the master bedroom was at the end of the hall. Mike opened the door slowly and I entered the room with him holding my hand. What an amazing room! A four poster canopy bed that was at least king size was the first thing that caught my eye. "Oh Mike, what a beautiful bed, I can't wait to try it out" I said as I pulled him towards the bed playfully. There was a slider to another deck off of the room and I was treated to a beautiful view of the golf course. I looked around and saw an easy chair, wall mounted flat screen and a few pictures on the wall. Against the wall at the foot of the bed were two sets of mirrored doors and an entrance to the master bath. Against the foot of the bed was a wooden chest with a padded top, which I figured to be a hope chest. He noticed my glance at the chest and said "yes, it is a hope chest and it is full of things that I have been hoping to share with someone special, and I think I have found her" he said as he squeezed my hand tightly. Mike pulled me up from the bed, anxious to show me his closets. The first one he opened and said "this is Mike's closet" as he slid the doors back to reveal a large walk in closet, big enough to have on whole side with double layers of clothing hanging. Suits, ties, shirts and casual wear on the left. On the right was a built in dresser with multiple drawers, as well as a shoe rack with many pairs of shoes. I could tell he was anxious to show me the other closet so I nodded my head, commented how nice it was and then followed him back out to the main room. The door in the middle of the wall led to the master bath and it had a double vanity sink, stand alone shower, whirlpool tub and a long mirror that ran along the top of the vanity. There was a closet that was full of towels and some toiletries. "Mike this is very nice and I think maybe what we need is a nice bath and to clean each other up" I said with a smile. He thought that was a great idea, but first thought we should look in Michelle's closet, to which I agreed as he grabbed my hand and pulled me back in to the bedroom. Mike stopped pulling me and grabbed me around the waist, and started to lift my shirt over my head. He wanted us to both be naked when we got in the closet, and I was more than happy to oblige. After I had removed my pantyhose, he asked that I keep my panties on and he did the same. He took my hand and slid open the closet door, threw the light switch and stepped to the side and made a sweeping gesture with his free hand. Pure feminine heaven! Michelle's closet was set up like Mike's but had double rows of dresses, skirts, blouses, night gown all in rainbows of colors, pastels, satins, silks and the shoe rack had 5 levels of shoes, boots and slippers. The dresser was full of lingerie: bras, panties, camisoles, half slips, corsets, pantyhose, stockings and garter belts. My cock was straining in my panties, now I understood why Michelle had wanted me to strip before entering the closet. I looked at her and she had a big smile on her face as well as a big boner in her panties. I turned back to look at the vanity and it was stocked with perfumes, cosmetics and there were three wigs on forms lined up on a shelf above it. The vanity was outlined with lights, like you would find backstage of a theater production. There were also two large jewelry boxes sitting on the vanity as well. "What do you think Teri?" she asked as she came and wrapped her arms around me from behind. "Michelle, I am speechless, what a beautiful assortment of clothing you have, you are very lucky" I said as she began to softly massage my cock through my panties. I could feel her cock pushing against my ass and I let out a soft moan of appreciation as I turned to kiss her passionately. We fell to the floor and got into a 69 position, both eager to please and horny for each others cock. I was in heaven, and from the sounds Michelle was making, she was there too! Knock, knock! "Dad, are you in there?" I heard from outside the bedroom door. Michelle let my cock slide from her mouth and she acknowledged that she was indeed in the bedroom and would be right out. "That is my son Tom, I will introduce you after I am done here" she said as she went back to work on my aching cock. I was too far into both giving and receiving to think about the implications; the only thing on my mind was getting myself off and tasting Michelle's cum too! We sat up and kissed, hugged and caught our breath after our orgasms. Michelle looked at me with a smile and said "Well I guess you will get to meet my Son sooner than we thought. Let's get cleaned up and see if he is alone or if he brought Steven or Stephanie with him. Michelle helped me to my feet and we both headed into the shower. After we were cleaned up, I started to put my male clothes back on, but Michelle would not hear of it. She handed me some clean panties and a satin shorty dressing robe in red and she put on a similar outfit in blue, took my hand and we headed towards the living room to meet Tom and maybe his partner too. I was very nervous especially since I was dressed in a woman's robe with panties underneath. No one other than Michelle had ever seen me dressed this way and I was slightly trembling, but Michelle gave me a reassuring hand squeeze as we made our way down the hell. "You will love Tom, he is a sweetheart and I hope he brought Stephanie too" she said as she pulled me towards the living room. Since we were in our bare feet, we did not make much noise as we came around the corner and found Tom sitting on the couch with his eyes closed and what appeared to be a woman kneeling between his legs performing a sensual blow job! Michelle and I stood there in our robes, holding hands and admiring the scene in front of us. I looked at Michelle and could see the bulge straining against the front of her robe and could feel my hard on rising too. Michelle let out a slight giggle and Tom's eyes opened and a big smile came across his face as he noticed the two feminized voyeurs enjoying the scene. "Sorry Dad, I got horny while I was waiting and Stephanie needed some nourishment" he said as he held onto Stephanie's head and fucked her mouth, never losing a stroke. Tom let out a slight moan as he shot his load and Stephanie groaned in appreciation as she swallowed it all eagerly. Chapter 5 Michelle and I watched as Tom stood up and gently pulled Stephanie up and gave her a kiss in appreciation of the blow job she had just given to him. As Tom pulled up his pants, Stephanie turned to say hello. She was a sissy knockout! She had a big smile on her face as she came over to give both Michelle and I a kiss hello. Stephanie was wearing a pink belly shirt that showed off her pierced navel and flat boyish chest, a pair of low rise blue jeans and pink accented sneakers. Her makeup was minimal but flawless, eyeliner, earth tone shadow, pink lip gloss and her hair was cut in a boyish blonde bob and her lipstick needed some attention after the blow job she had just completed! "I need to run to the powder room and fix my makeup" she shrieked as she ran down the hallway. Tom came over and gave his Dad a hug and kiss on the cheek. "So, this must be Teri? The one I have heard so much about over the past weeks?" He said as he turned to give me a quick hug too. "Yes, this is Teri and we have become the best of friends and I'm glad that you are able to meet her today, I'm glad you and Stephanie stopped by" said Michelle. Stephanie came back into the room and Tom introduced me to him. Stephanie had fixed her lipstick and hair while she was in the bathroom and she was a very cute guy/sissy, I could see that she and Tom cared for each other very much, they made a cute couple. She commented on the outfits that Michelle and I were wearing, saying that the dressing gowns "were to die for" with a cute giggle. Tom took Stephanie by the hand and started to pull her towards the door. "Come on baby, let's leave these two alone so they can get back to what they were doing" he said with a smile. I must have turned beet red but was quickly put at ease as Michelle grabbed my hand and we walked with them to the front door. Michelle invited them back for dinner the following Saturday, to which they quickly agreed. After more hugs and kisses all around, they left and it was just Michelle and I once again. Michelle took me in her arms and kissed me deeply. "Teri, I am so glad you go tot meet Tom and Stephanie, I was hoping that I would get a chance to show you off and it happened, I hope you weren't offended seeing Stephanie sucking on Tom's cock" she asked. I assured her that I was not offended at all and it actually turned me on to see how much in love they were and I thought it was a beautiful thing. Michelle turned on the oven to let it get warmed up for pizza and then suggested that we slip into something more comfy. She poured us both a glass of wine and we went back to the bedroom to choose our evening wear. To be continued.....? Footnote: Hi everyone, I have been away for a while (life does have challenges!), any comments or recommendations would be appreciated, or just a note saying hi! Contact me at [email protected]. Hugs, Teri Franken