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BOTH WAYS by Barbara (My fifth story) This story is in two parts. There is very little CD/TV in part I. Even if you want to skip to Part II, you should skim Part I. It is a setup to Part II and explains how the characters got where they are in the story. PART I My name is Edward, Edward Wister. My friends call my Eddy. I was 18 the summer I graduated from high school. Neither me nor my best friend, Sparky, were totally experienced sexually, but we were not nerds either. I had been on a few dates and actually touched my date's boob for a second before getting my face slapped. I still remember that it was in the back seat of a Ford. Sparky, otherwise known as Samuel Parton Kaly (SParK), had an interesting family. He had an older sister, Alice, whom I hardly knew. His mother had died when Sparky was 10. His dad had remarried four years later to a young woman of 26. Carolynn Kaly was now 30, and Mr. Kaly (Thomas) was 48. To someone who is 18, anyone over 22 looks ancient, but I have to be honest. Most people would have seen Carolynn as young, vivacious and very attractive. Just prior to high school graduation, Mr. Kaly had started a remodeling job in the back yard. Sparky and I had both put some serious labor into the project. The job was unfinished at graduation when Mr. Kaly decided that Sparky needed some college preparatory schooling and sent him off to some prep school in New England. Somewhat against my better judgment, I volunteered to work on the project as long as I could. Mrs. Kaly only worked mornings, and I made arrangements to meet her at the Kaly home early on a Monday afternoon. I was already on the front porch when she drove up and shouted through the car window that she would come around and open the front door for me after she parked the car in the garage. A few minutes later, the large front door swung open. Mrs. Kaly had a very upscsale opinion of what constituted proper business attire for her office. She was standing there in a classic black sleeveless dress with a jewel neck line and a hem just above the knees. She had two inch black pumps, and her blond hair was stacked up elegantly on her head. It was in complete contrast to me, who was wearing a tshirt, cutoff jeans and a pair of old tennis shoes with no socks. "Please come in, Eddy. Everything is waiting for you in the back yard," she said. "Thank you, Mrs. Kaly," I replied. "I think I know my way." "I'm sure you do. It's right out the back door, just like always." Mrs. Kaly headed off through the family room with me right behind. She made a turn to go down the hall, and I started to go around her to reach the sliding glass door to the back yard. As she turned to go down the hall, she asked, "Edward, can you help with something for just a minute?" "Oh sure, Mrs Kaly, but you can call me Eddy if you like." "Edward sounds so much nicer, don't you think? Anyway, follow me." She walked down the hallway and stood at the door to her and Mr. Kaly's bedroom. "Edward, I can't reach my zipper. Can you undo me?" She turned her back to me revealing the long zipper down the back of her dress. "Don't be bashful. I need to get out of this dress and into something so that I can help you." "Mrs. Kaly. Well, I........uh," I stammered. My face must have been beet red by that time, and I was more than a little embarrassed. "Now Edward, just reach up and pull it down," she said in a firm voice. With some hesitation and a little excitement, I reached up and took the zipper clasp in my fingers. I pulled the zipper down a few inches revealing a little of the smooth white skin behind it. "Is that enough?" I questioned, hoping she would say, yes. "All of the way Edward. It is such a reach to pull that thing down." I renewed my efforts and pulled the zipper down as far as it would go stopping just above the point where her rear end flared out making the back of the dress look full. Her arms came down for an instant, and before I could think, the dress was lying in a black circle at her feet. She turned to face me wearing only a red bra, red panties under black panty hose and her two inch heels. Her arms quickly enveloped me, and my dick went to attention quicker than it ever had before. I barely managed to say, "Mrs. Kaly, I think I had better go." "Now, now, Edward. What would your mother say if I called her and told her how embarrassed I was when you came into the hall unexpectedly and looked into my room seeing me like this? She would be very upset." "But that's not what happened," I responded with a little bit of panic. "When's the last time your mother believed anything you said? She'll be aghast. You will be grounded forever. She didn't raise a voyeur. Besides," she said as she placed her hand against my straining erection, "I think you're ready for some fun." My head was full of concrete. I knew right from wrong, and this was something society said was wrong. You do not play games with married women, especially your best friend's stepmother. But I wasn't thinking with my head, I was thinking with another part of my anatomy. The only thing passing through my mind was, "I'm gona get laid. I'm gonna get laid." She took my hands in hers and stepped backwards out of the dress lying at her feet, pulling me along with her. We were in the bedroom, and she looked at me and asked, "Have you ever been intimate with a girl before, Edward?" "No, Mrs. Kaly, no I haven't." "Then I want you to do only what I tell you to do. I don't want you popping off early before I can have any fun. Do you understand?" I could only shake my head up and down. "Good. Now, first, while we're in the bedroom, my name is Carolynn; but as soon as we leave the bedroom, I'm Mrs. Kaly again. This is our little secret, and I don't want anyone getting suspicious. Do you understand that?" "Yes, Carolynn," I replied. "Oh, you are a quick learner Edward," she said. She moved her hands to my waist and grabbed each side of my tshirt lifting it up to my armpits. "Help me a little to get this thing over your head." I moved my arms up, and the tshirt was soon on the floor against the wall. She moved her hands down my chest and grabbed the button on my shorts. She deftly opened the button and pulled the zipper down. She bent over as she pulled my shorts to my ankles leaving me in my briefs with a bulging erection peering over the top of the waistband. With a few efficient moves she had my shorts and my tennis shoes lying beside my tshirt. "Now, Edward, I want you to put your hands on my shoulders." I put a hand on each shoulder. "Good, now how does that feel?" "Just fine," I answered. "Now, pull me just a little bit closer, then reach behind me and undo the clasp." She didn't have to tell me which clasp. I reached behind her and felt the clasp of her bra. I had to figure out what clasped into what, and I fumbled a little. She stood there patiently waiting for me to learn. Then the bra snapped a little when I finally got the clasp undone, and, with a brief shirk by Carolynn, it was lying on the floor too. I had never seen a woman's boobs in the flesh before, and I almost came right then and there. Carolynn noticed my excitement and said, "Deep breaths, Edward, deep breaths." We stood there for a while longer until I had calmed down. Carolynn was taking this nice and slow and was trying to keep me from cumming too early. After a minute or so, she turned to the bed and sat down on the edge. She laid herself back and kicked off her heels. Then she put her hands on the hem of her pantyhose. "Help me pull these off, Edward," she said in a soft voice. I approached her and put my hands in the hem alongside her hands and began to work the pantyhose down her thighs. "Be sure to get my panties at the same time," and I reached my fingers inside the red panties working them down to her knees along with the panty hose. She sat up again and said, "Now grab the toes while I work everything off. I don't want them inside out." I grabbed the toes of the pantyhose and gently pulled as she worked the hose and panties down the last few inches of her legs. OH BOY, there I was in the same bedroom with a naked woman lying on the bed in front of me. She moved over to the right side of the bed and motioned beside her. "Lie down. Get comfortable." I didn't have to be told twice. We were side by side, her totally nude and me still in my briefs. "Do you know what foreplay is?" she queried. Well, I didn't really, but I took a stab at it and said, "Touching each other and playing around with your hands before you do anything else." "Kind of. Except here, you are very young and inexperienced. If I used my hands to play with you, you would ejaculate well before I even started to get warm. Have you ever ejaculated when you were with a girl? You know, shot your wad? It's nothing to be ashamed of really. I'd like to know." I had, but I didn't want to admit it. On the other hand, I didn't want her kicking me out of bed when I was so close to scoring. Somewhat sheepishly, I answered, "Yeah." "Good, but I don't want you shooting your wad until later when I can enjoy it. Because you're new at this, I really don't expect more than a stroke or two out of you, but I at least want that. What we're going to do is you're going to play with me before I play with you. I don't even intend to touch you for a while. This will get me warm and, hopefully cool you down. And then we can enjoy each other better when we're ready for..... You know." She bumped me slightly with her elbow and smiled broadly as she spoke. She took my hand and put it on her stomach as she lay flat on her back. "Just hold me there for a while," she said in a very relaxed tone. After a few minutes, she spoke again, "Move your hand up slowly and gently until I tell you to stop." My hand went up her stomach, it approached her breasts, and it finally reached the cleavage between those two luscious mounds. "A little to the right," was her next instruction. My hand was soon on her nipple, and she put her hand on mine gently guiding me around and around her right breast. "Gently, gently," she whispered in an obviously satisfied manner. Carolynn began to breathe deeply. She closed her eyes and looked quite contented as I continued to massage her breast. "Edward, move you hand down now." I moved my hand off of her breast onto her lower chest and down across her belly button. "Lower. And gently," she said. I thought I knew where I was going and kept my hand moving onto her abdomen and then into her pubic hair. (I had never touched pubic hair before, except mine, of course.) Soon my hand was between her legs as she said, "And the finger goes in and up." I felt the loose folds at the entrance to her vagina. I gently pulled the folds apart and put my middle finger into her. She gasped slightly and then pursed her lips. She laid her hands on my hand and positioned it just right so as to give herself the most pleasure, and then she started pumping my finger in and out of her. "Like that. Can you do it like that?" she asked. I just kept pumping my finger in and out, "Yeah, like that." The words came out quickly. Her mind was between her legs and she did not want to interrupt her concentration on her clitoris. Carolynn started to pump her whole body, pushing vigorously against my finger. Her breathing became shorter and somewhat labored. She took her hands and placed them on either side of my head pulling it toward her. She positioned my mouth just over her left breast and said, "Lick me." I stuck out my tongue and licked around her nipple. "Oooooooooooh, Ooooooooooooh, Aaaaaaah. Suck it, Edward, suck it," she commanded. The voice was no longer sweet, it was demanding. I lowered my head and took as much of her breast in my mouth as I could. And, I sucked. Carolynn went into convulsions. She moaned and sighed and clenched her teeth. She arched her back, grabbed my hand that was in her pussy and pushed hard. Her face turned bright red as if her blood pressure had gone way up. She kept her back arched for a few seconds looking as if she was savoring every moment. Then she relaxed only to start the cycle again as she kept up the pumping rhythm on my finger. She grabbed my head again and said, simply, "Other boob." I started to suck her right breast while she took a free hand and caressed her left one. Again, she started to pump ferociously against my finger, then arched her back, sighed and held the position for a few seconds before relaxing. She was having one orgasm after another, and I was the cause of it. I took a little pride in that. I continued to pump Carolynn with my finger while sucking first one breast and then the other for about 15 or 20 minutes. She had an orgasm every two or three minutes at first, but then it tapered off. Quite frankly, I was starting to get a little tired. Her pussy had gotten slobbery wet. Finally, she relaxed, pushed my head off of her breast and pulled my finger from her love canal. She took her hand and pushed my shoulder down until I was flat on my back, put her fingers into the waistband of my briefs and pulled them down to my knees. She sat up and pulled the briefs off, motioning me to lift my legs to make it easier for her. My briefs were soon lying on top of my shorts, and my erection was exposed for her to see. She took a long look and smiled. Carolynn mounted me and put her hand between her legs. I could see that she was using two fingers to open the folds of her vagina and was using the others to search for my prick. She lowered herself down my abdomen and guided my shaft into her. The head of my penis entered her easily. Oh, brother did that feel good. I was inside. I was actually inside a woman. She lowered herself some more so that my whole shaft was inside her. I could hardly restrain myself. I needed to ejaculate, but I wanted it to last forever. The only thing Carolynn could say was, "Hard dick, hard dick. Oh that feels good, hard dick." She was right, I lasted about three strokes before cumming as I had never cum before. It did feel good. I grabbed her ass with both hands and tried to push her as far as possible onto me. It was difficult from underneath, but I pushed as hard against her pubic bone as I could. And then it was over for me. I had shot my wad, and I was exhausted and contented. "I felt you pop in me, Edward," she said as she looked into my face. "You'll be hard for another minute or so, so just lie still." She continued to pump against my still swollen shaft for another minute, until I had gone flaccid and then she stopped. "No talking, Edward. Never ask your partner if she enjoyed it. You should already know. Just lie here for a while." After a while, Carolynn pulled herself off of my now limp organ and stood on her knees over me. Everything in her vagina began to drip onto my stomach. She chuckled. "I just wanted you to see what we girls have to go through to satisfy you guys. I'll drip for another 15 minutes or so and will have to wear a pantyliner when we go out to work on the project." She grabbed several tissues from the box near the bed and put two under her still dripping pussy. "Don't leave a wet spot. Don't drip anything." She tossed me a few tissues. "Wipe up that stuff on your tummy and use one to keep your dick from dripping." "Uh, OK," I replied. Carolynn rolled off of me and stood by the bed. "Come on, we need to shower." Shower, I hadn't thought about that. We needed to get this goo off of us. I rolled out of bed and Carolynn reminded me, "Keep that tissue on the end of your penis so that you don't drip." "OK" She led me to the bathroom and turned on the shower. "Get in, I'll be right back." I got in the shower and started to lather up. In a few seconds, she had returned and entered the shower with me. "Scrub me down, Edward." "My pleasure, Carolynn." I grabbed the soap and began to rub it over her body. She handed me a wash cloth . "Don't forget between my legs." I lathered up the wash cloth and bent down a little to clean her up at the entrance to her pleasure palace. We dried off using the same towel. Carolynn didn't want to explain to Thomas, her husband, remember, why there were two wet towels. We stepped out of the bathroom back into the bedroom. My shorts and tshirt were still there, but my briefs were missing. What I saw was Carolynn's pair of red panties sitting there on top of my shorts. "Looking for something?" she asked. "Yeah, my briefs. I thought they were right here with my shorts." "This was your first time, right?" "Yeah." "Then they're not your briefs anymore. They're mine, by right of conquest." "What? What will I wear?" I asked pleadingly. "Edward, the briefs are mine. By right of conquest, the red panties are yours." "Mine? I can't wear your undies. I'm a guy." "Edward, nobody will know except you and me. You either wear the panties or you wear nothing under your shorts. Won't that look silly with that hunk of meat," she pointed to my dick, "unchained and bulging against that flimsy pair of shorts. The panties are a little small for you, and it will be a tight fit, but just pick them up and put them on. Be sure to get the tag in the back. ....... Besides, I think it's cute." Her last statement got me. If she thought it was cute, I was all in favor of it; anything to stay in her good favor. My mind was totally driven by sex. I picked up the panties and timidly put one foot in at a time. They were a little tight, but I got them up where they belonged. Then, a strange thing happened. I thought I would be revolted by wearing the panties. Instead, my dick started to get hard again. Very quickly, it was poking out of the panties in Carolynn's plain sight. "Well, well, well, you seem to like that," Carolynn said mater-of- factly. I was thoroughly embarrassed and said so. "Embarrassed," she exclaimed. "What's to be embarrassed about? It's cute." With that she came over and touched my dick through the silky fabric of the red panties. Oh what a rush that was. I groaned, and she smiled. Then she bent over and went to her knees. She pulled the front of the panties down and took my dick in her hand. She opened her mouth, covered her teeth and put me in her mouth: oh, what a feeling. She bobbed up and down. She was still wearing the lipstick she had on when she first pulled up in the car, only now she was leaving it all over my erection. She pulled off and said, "Put your hands on my head and GENTLY maneuver me so that you enjoy it the most." My hands were on her head in an instant and gently pushed and pulled until I had her bobbing where it would do the most good. I could feel myself tensing and suddenly I was exploding in her mouth. She didn't flinch, and I could see her swallowing every drop of my cum. She pulled off as I deflated and licked the last drops of ejaculate on the tip. I started to go to the bathroom to cleanup again. Instead, she stopped me and handed me some cloth gizmo. "It's a pantyliner. I'm wearing one, because I'm dripping. You can wear one too until you stop dripping. Only, you'll have to wear it a little higher. As for the lipstick, leave it alone. It will remind you of me when you get home." I took the pantyliner. I had seen these before on my mom's dresser, but I didn't know what they were for. I watched Carolynn pull up her panties and simply slip the pantyliner inside. I put mine inside my panties but a little higher so that it would catch the stuff still dripping from my dick. From watching Carolynn, I knew that it was designed to be worn between the legs rather than where I put it, but, oh well. My anatomy was different. I picked up my clothes and started to get dressed. I was also watching Carolynn get dressed. It was interesting, I had never seen a woman dress before. She saw me watching her and smiled. It was entertaining, especially when she bent over to get her boobs inside the cups of her bra. I got back into my shorts and tshirt. Carolynn was wearing jeans, a flannel shirt, a large sun hat, sturdy boots and gloves. She still looked attractive. I turned to leave. "Edward, a few things before we go out. Remember, as soon as you go through that door, I'm Mrs. Kaly again. No mistakes. We must be careful. OK?" "Yes, Mrs. Kaly." "You learn so quickly,,,,Eddy. Also, bring your panties back tomorrow. I'll store them her. Whenever you want a little something extra after our 'fun,' we can bring them out for you." Tomorrow. She wanted to do this again tomorrow. I was truly hooked now. She could have told me to rob a bank, and I would have done it as long as I was able to get inside her again. "And, Eddy, I like you very much. You're a very nice person. I wouldn't do this with just anyone. But, this isn't love, it's just a fling, an affair. Let me blunt for you. To me, you're a very good friend with a hard erection. To you, I only want to be a very good friend with a warm pussy. Understand?" I was a little crushed, but at least I was her friend. "Yeah. I understand," I answered. We spent the next several hours raking decorative rock, digging holes, pruning, edging and watering. Finally, the telephone rang, and it was my mother wanting to know if I was coming home for supper. I got home, hid my red panties in my dresser for overnight, took a shower and had dinner. I spent the next two weeks balling Carolynn five days a week, Monday through Friday. On the first Thursday, she finally let me get on top explaining that she thought men lasted longer on the bottom and that she had kept me on the bottom until I established some endurance. We also began kissing during foreplay with Carolynn trying to suck the skin off my face. For an encore, one of us would often reach for the red panties which Carolynn had pushed into a corner of a drawer. I found myself pulling them out as often as she did. Carolynn always obliged with a beautiful blow job. Lying in bed one day after I had filled her with my cum, I told her that my parents were planning a month long European vacation later in the summer. Now that I was 18, they could legally leave me by myself and were planning the trip in honor of the event. I could see Carolynn's eyes sparkle as I told her, but I had no idea at the time what she was thinking. On the second Friday, she told me that she was planning a small party in a few weeks to celebrate the completion of the back yard. It would be held the week before my parents left on their vacation. She said she wanted my parents to come. Then, she said, "Edward, we only have one more week on this project, probably less. I'll still need you next week, but we won't have any treats on Monday." "Why not?" I asked, somewhat surprised. "Edward, I'm a woman. Monday is that time of the month. Do you understand a woman's cycle?" I didn't really, but I said, "Kinda, but not a whole lot." "Edward, I get a period every month. Monday is it, unless I'm pregnant, of course." I must have turned 27 shades of ash and white. My brain yelled at itself, "Yeah, Eddy, girls get pregnant when you fuck them without a condom. Where's your brain been the last two weeks, you moron." Carolynn stared at me and giggled. "Oh Edward, you should have seen yourself when I said 'pregnant.' But, don't worry too much. I'm on the pill." She put her hand on my shoulder and said, "Be sure to ask your girlfriend when you get to that stage." Carolynn and I had one more bedroom game the Friday after her period ended. It was also the last day of work on the backyard which meant that I had no excuse to come over to her house anymore. She described her plans for the party the following Saturday and told me my parents had accepted the invitation. I was hoping that a month alone would give me plenty of opportunity to continue my relationship with Carolynn. PART II Carolynn and Thomas threw a modest party in their new backyard for the neighbors and Thomas' business associates. I had only met Thomas a few times before and always when Sparky was there. He was a rather large man without an ounce of flab on him. He was also on the intimidating side, and I kept my distance. Carolynn struck up a conversation with my mother about her European vacation. She assured Mom that she and Thomas would keep an eye on me and asked if it was alright for me to spend a few nights at their house to get a warm meal if I wanted one. Mom thought that was a capital idea and thanked Carolynn for her interest. "It's the least Thomas and I can do considering all of the help Eddy has been to us," Carolynn told my Mom. Again, Mom was thankful. She also mentioned that Tom might be able to get me a summer job for the remainder of the summer at his consulting firm. I took my parents to the airport on Friday morning and was at Carolynn's house with my duffel bag when she got home from work early Friday afternoon. I was expecting a good time. Carolynn let me in and took me back to the bedrooms. "Sparky's room is a mess. It really can't be used, but Alice's room is in good shape and ready for you," she said. "Alice's room? Uh, not Sparky's? You want me to sleep in his sister's room?" "We started remodeling Sparky's room and Alice's is the only one available. You do want to be close to me, don't you?" "Well, yeah," "Then come with me." She turned and opened the door to Alice's room. It was definitely a girl's room, lot's of lace and pink, red hearts, stuffed animals, that kind of thing. There was also a pair of red panties lying on the bed with a matching red bra just above it. "The panties look new," I said. "They are. I bought them just for you, and they're in your size." "And the bra?" "Edward you always have to be changing things if you want to keep your love life fresh. I figured that if the panties made you hard, panties and a bra would make you harder. Want to try them?" she asked. As always, I was thinking with something other than my brain and said, "Yeah, I'll try it." I stripped off my clothes and began to reach for the panties when Carolynn said, "Before you do that, come with me." I was totally nude, but having balled Carolynn some fifteen times, I was not ashamed at all of my condition. "Where are we going?" I asked. "With me. Come." She led me across the hall through her bedroom to the bathroom and instructed me to get into the shower. She put on two rubber gloves and took a bottle from the counter which said, "Nair." "Carolynn, that's Nair. It takes your hair off." "Of course it does, Edward. I want to give you even more of a pleasurable feeling by letting you wear a pair of pantyhose too. The only thing about pantyhose is that you need to wear it on clean legs to get the best feel. It doesn't feel right on hairy legs." I knew I wasn't going to get inside her if I objected too much so I stood idly by while she lathered up my legs. Then she went to my chest and my arms. I thought that was a little much, but ten minutes later my hair was circling down the drain. I spent the next half hour or so showering and trying to get that chemical smell off my body. Carolynn finally announced that she thought the smell was all gone. As I stepped out of the shower, she gave me a razor and some shaving cream along with instructions to get a close shave. My beard was not full yet, but a few minutes later, it was nonexistent. We went back to Alice's room where I donned the red panties and got the anticipated arousal in my now hard penis. Carolynn handed me the bra and helped me clasp it behind me. As always, Carolynn was right, it gave me another rush. She added to the excitement by pulling two falsies from one of Alice's drawers and placing a falsie in each bra cup. She pulled a pair of new black pantyhose out of its wrapper, told me to sit down in the chair, and handed the pantyhose to me. "It's just like a pair of tight socks. You have to roll them up to the toe and then roll them up your leg. Because they're new you will have to pull them rather tight as you roll them up your leg." I rolled up one leg and slipped it over my toe and up to my ankle. Carolynn told me to stop and had me roll up the other leg to the ankle also helping me pull the fabric tightly. I then rolled the first leg of the pantyhose to my knee. OH, what a feeling that was. It was the most erotic sensation I had ever had from a piece of clothing. It encased my leg and constantly caressed it. The other leg was the same way. I was hardly able to contain my pleasure. Carolynn only said, "See why I had you clean your legs?" Carolynn had me stand up to pull the pantyhose to my waist. At first, I could not get the crotch of the pantyhose all the way up to the crotch of the panties. At Carolynn's instruction, I rolled them down to just below the knee again and pulled them up a second time getting a much better fit. "Edward, I want you to sit back down in the chair, and I don't want any questions. I'm in charge. Understand?" Carolynn was always in charge. I just shook my head up and down and sat down. She reached for a small pair of scissors and began to trim my eyebrows. She then put some heavy wax on them. Next came a tube that was on Alice's dresser. She began to apply the contents to my forehead and face. First it was a paste of some kind that she rubbed in until it was thin, and then she brushed powder over the paste. She pulled out a pencil and began to mark around my eyebrows. The eyes were next. I soon had a false eyelash on each eyelid. She took a small case from the dresser, opened it, and rubbed the small brush in blue powder which she applied to my upper eyelids. There were three colors in all which she brushed together with another small brush. Then came a tube of black stuff which she ran in a line just above my eyelashes. The last item for the eyes was to brush each eyelash, upper and lower, from a tube labeled "mascara." Carolynn spent another few minutes applying more of the paste and the powder on my cheeks and chin. She opened up another small case with redish powder and put it on my cheek bones. I knew what the last stuff was. It was lipstick, and Carolynn used another brush to apply it. She had me pucker up and then open my mouth as she took great care to apply it just so. She handed me a tissue and told me to bite it with my lips. I left a big red stain, and Caolynn threw the tissue away. In all, we had been almost two hours since I first went into the shower. What I would do for sex. Carolynn handed my a full slip. "Let me help you put it on. I don't want to ruin your face. We can't have any fun if you ruin your face." She rolled it up and slipped it over my upright arms. She had me turn my face to one side as she pulled it past my head. The straps sat on my shoulders, and she brushed the rest of the slip down until it hung just above my knees. I had not noticed the black dress hanging on the door to the closet. Carolynn took it off of its hangar and unzipped the back. "You can put it on yourself, but you will need help with the zipper. We both know that, don't we?" She smiled as she said it. I pulled the back apart and put one leg and then the other in the dress. I pulled it up to my shoulders and put my arms into the armholes Carolynn zipped me up and secured the clasp at the top. The dress was similar to the black dress she had worn the day she first seduced me except it had quarter length arms and a hem that went below my knees. There was a shoebox under Alice's bed which Carolynn now pulled out. Inside was a pair of black suede pumps with a 1 ?" heel. They were in my size and Carolynn had me put them on. I wobbled for a while but soon had my balance. She told to me to walk around a little to get used to wearing them. In a short time, I was walking fairly well in them although I did tend to stumble every once in a while. I also noticed the sound of the pantyhose on one leg brushing up against the pantyhose of the other leg. We walked back into Carolynn's bedroom where she disappeared into a walkin closet. She came out with brunette wig. "Your coloring is naturally dark, and a brunette color will look a lot nicer than blond," she stated. She sprayed the wig and combed it out before putting it on my head. "Almost finished." I breathed a sigh of relief. She had me stick my arms out in front of me. She took a perfume bottle and sprayed the back of each wrist and then my neck. She had me sit next to her vanity and instructed me to put my hand on the vanity top. I soon had eight fingers and two thumbs with a stylish covering of red fingernail polish. "No girl is complete without jewelry." She took two clip on earrings from her counter and put one on each ear. They looked like diamonds but were probably cut glass. They dangled just over an inch below each ear. There was a four string pearl choker that she put around my neck and clasped in the back. On my right arm she put a bracelet of dark blue stones and a woman's watch on the left. "Finished. Want to see the final product?" she asked. I did not really care to see, but I thought I had to. She took me to a full length mirror and had me stand in front of it. There, staring back at me was a young girl my own age. She wasn't the most handsome girl I had ever seen, but it was definitely a girl. Her hair was straight and came down just below her shoulders. She was quite elegant in the black dress, black hose and black pumps. "It's a girl. That's not me," I said. "It's you. And in a few minutes we can have some fun. But first, you need a name. Eddy just won't do for a pretty young thing like you. How about a favorite name of mine, Barbara? Is that OK?" I shrugged my shoulders. "Barbara it is," exclaimed Carolynn. "Now, Barbara, why don't you go in the front room and watch a soap opera like a good girl while I get ready?" "Ready for what? Why did you do this to me?" "I did it for fun, just good clean family fun. Now go watch TV, and I'll explain more in just a little while. OH YEAH, call me, Auntie Carolynn. Amuse me a little." I went into the family room and turned on the TV. I wasn't about to watch any soap opera. I tried to pick up a ball game on the cable. Thirty minutes later Carolynn came in dressed in the same black dress she had worn on the first day. She sat beside me on the couch and put her arm around me. "Barbara, I have some different sexual proclivities. I like girls as much as I like guys. What I like best in a girl, though, is what you have between your legs. I get a substantial amount of enjoyment out of doing it with someone who acts like a girl but can still enter me." This was truly weird, but I simply said, "Oh." "Now let me try to teach you how to act like a girl so that we can have 'fun' in a little while." We spent a long time chatting about things that meant nothing to me, really. But she taught me how to hold my self, how to sit and how to speak in a soft voice. After a while she asked if my erection had deflated, which it had. She helped me pull my dress up and my panties down to tuck my manhood into the panties where it couldn't be seen. I lost track of the passage of time. Suddenly the door to the garage opened, and Thomas walked in. I was terrified. Carolynn took it all in stride. "Oh Tom, I want you to me my niece Barbara. I told you she would be spending the night tonight." Tom walked over and offered his hand. Carolynn had taught me that most women shake hands like a wet rag, so I shook hands very limply. "How are you Barbara?" he asked. In that soft voice Carolynn had taught me, I replied, "Just fine, uncle. It's nice to meet you." So far, he did not seem suspicious that I was anything other than Barbara. I just kept praying that I could keep up the illusion. I was irate at Carolynn for letting this happen. Of course, I was beginning to get the impression she had planned this. "Is everyone ready?" asked Carolynn. "I am," was Tom's response. "I need to go to the back and take care of one thing. I'll be right back." "Good. Barbara, I moved your purse over to the coffee table there. Pick it up and we're ready as soon as Tom comes back," said Carolynn. Purse, what purse? There was a black purse on the coffee table. And Carolynn was pointing to it. I must have looked puzzled. "I told you we were going out to dinner as soon as Tom came home. Now pick up your purse and let's go." Tom disappeared down the hall, and she moved closer speaking in a whisper. "Tom is expecting to take me and my niece, Barbara, to dinner. Either you come or there'll be all hell to pay, especially if he finds out who you are and how you got this way. Now let's go." I picked up the purse and slung it over my shoulder. Tom reappeared, and I was soon in the back seat of his Mercedes headed off for some swanky restaurant. Fortunately, it was getting dark, and I did not have to walk around in broad daylight. I kept quiet during the drive but almost panicked again when we had to walk through a parking lot and an entranceway crowded with people. No one was noticing me, however, and I began to relax. As we waited to be served, Tom kept trying to engage me in conversation. I tried to keep my answers brief always remembering to use the soft voice Carolynn had taught me. Carolynn ordered some girlie salad and suggested that I try it too. I would have preferred a steak, but I took Carolynn's suggestion. I let Tom do all the ordering because I wanted to do as little talking as possible. I did not want my voice to betray me. The salad was a real girlie salad. It wasn't that it tasted bad, but that it wasn't filling. I was a guy and needed some meat. We finished dinner and ordered a dessert. Carolynn then turned to me and said, "Come with me and bring your purse." She got up from the table, and I followed her. I did not know where she was going at first, but she went straight into the ladies room. I wanted to call out and say "no," but she was already inside. I tried to keep my heart in my chest as I followed her into that forbidden place. The room was empty except for the two of us. She turned and said, "You've been fidgeting for a while. Go in a stall and do your business. Remember to sit down so that no one else coming in will get suspicious. And also remember to wipe yourself. All girls wipe themselves." When I got out, she had her lipstick out and touched me up in a few spots. "That's better. Let's have dessert." We finished dessert and Tom paid the check. As we left the restaurant, Tom said, "My office is right around the corner. Barbara might want to see my office. There is a fantastic view from the 20th floor." I did not want to go to Tom's office, but Carolynn said "yes." And we were off. Two blocks in heels can be painful if you are not used to them, even if the heels are only 1 ?". By the time we got to Thomas's building, I was developing a blister or so I thought. At least, I thought my toes would soon mutiny on me. Thomas waved to the security guard, and we walked toward the elevator. Approaching the elevator, Carolynn's cellphone rang, and she fumbled through her purse to find it. She pulled it out and had a brief conversation with someone who appeared to be irritated. She hung up and turned to Thomas, "It's my boss, Michael. I need the keys to the Mercedes. I'll be right back." Thomas gave her the keys, and she left the building. Thomas and I went up to the twentieth floor. Thomas' office was indeed spectacular. He had done well as a consultant. His firm took up the entire floor, and Thomas had a large office in one corner with several large windows overlooking the city lights. It had the customary large desk and cushy chairs as well as a very large sofa looking out through the windows. "I like to sit there to gather my thoughts." He said as he motioned to the sofa. He put his hand on my shoulder and guided me toward the large windows overlooking the city. We walked over to the widows with his hand still on my shoulder. He stood behind me and pointed out a few of the prominent buildings with his free hand. He was tall and stood a head taller than me and could see over me. Then he put his free hand on my other shoulder and moved both hands down to my upper arms and squeezed me gently. His head came down and, and he put his face came in close to the back of my neck. "I like your perfume." Shivers went through my body. He was making a pass at me. I had to do something, but I couldn't say I had to leave. There was nowhere to go. Carolynn had taken the car, and I couldn't walk home, at least not in these heels. He must have felt me shiver and said, "I'm not so bad. I can be very gentle." "Uncle, this isn't a good idea. Auntie Carolynn could come in at any time." "I don't think she will." His nose was almost in my ear and I could feel his breath on the side of my face. "Besides, I think she's two- timing me anyway with that kid down the street, Eddy what's his name. If she comes in and sees us, I'll just threaten to divorce her for playing around. That'll teach her and that kid. It'll be a messy divorce, and his name will be on the front page of every paper in town. She won't want that." His voice was very soft and he still had his hands on my arms. I was really starting to have some fear. If he got more personal, he would find out what I was and who I was. He may have already figured out that I was wearing a wig. If he got his hands between my legs, he wouldn't find what he was looking for. Who knew what he would do. But things didn't play out as I anticipated. He whispered this time. "Now, you don't want Eddy's name on the front page of the paper, do you?" "No." I responded softly lowering my head in resignation. "I didn't think so. Carolynn told me all about you. She thought you were very close to Eddy, his alter ego so to speak." "She told you all about me?" "Yes, I know who you are and what you are, though I wouldn't have known if Carolynn hadn't told me. She did a very convincing job on you. Tonight is her effort to keep me from divorcing her after I found out about her and Eddy. She thought that Eddy's friend, Barbara, would help me out to keep Eddy's name out of the papers. You can leave, you're free to go. But, if you do, I'll start divorce proceedings tomorrow naming Eddy as my wife's lover." He stressed the word "friend." He knew who I was and what I was. I just stood there with him holding me. What did he want? "Let's sit on the sofa. You need to get off your feet." He turned me in place and nudged me toward the sofa. He sat down and pulled me down beside him. Immediately one arm went over my shoulders and his free hand took one of my hands in his. We sat there for a while, while I contemplated how I had gotten myself into this mess. Here I was, dressed as a girl, sitting on a large sofa with an older man who was imposing himself on me sexually. Where would it end? I didn't have long to wait. He looked at me longingly and said, "Carolynn says that you kiss very well." He put his face in front of mine and pecked at my lips. I sat there impassively. "Come, come, Barbara, let's get a little response." He pecked again, and this time I pecked back a little, more out of fear than anything else. He took the opportunity to kiss harder. He pushed his tongue against my lips, and I just opened up for some reason. He began to suck like Carolynn had taught me, and I sucked back. Our tongues darted back and forth, and I felt like my lips would fall off. I was kissing a man. I couldn't even close my eyes and pretend it was Carolynn. I could feel his stubble the entire time we were kissing. I couldn't believe what I was doing. He was still holding my hand. He pulled it toward him and placed it on the zipper of his trousers. I could feel his erection underneath, and I tried to pull my hand back. He held me tightly on his manhood, however, all the while kissing me madly. He pulled back for a second and said, "Pull the zipper down, now. Open my pants up." I was totally in fear of this bear of a man. I grabbed the zipper and pulled it down. He took my hand and slid it into the fly so that I could feel his swollen member in his underwear. "Now the button, Barbara." I meekly obeyed opening up his trousers. He raised himself a little and looked at me. "You know what to do." I pulled his pants and his briefs down exposing his erection. Then I figured out why Carolynn had said "Hard dick, hard dick" when I was inside her. Thomas had a large organ, but it wasn't very hard. It probably wasn't hard enough to get inside his wife. She needed someone to satisfy her, and she had selected me. I was now paying for the privilege. He took my hand and placed it on his dick. I started to rub him like I knew he wanted me to do. He started to moan with pleasure. Then, a strange thing happened. Instead of being revolted, I took pleasure in giving him pleasure. He put his hands on my head and began to push me down. I resisted at first, but he pressed harder. I relented and was soon staring his love shaft in the face. I stuck out my tongue and licked the shaft up and down. He groaned with satisfaction and said with a few gasps, "Inside, take me in your mouth." I took his organ in my hand and placed it in my mouth. He was sighing and gasping like I did when I was inside Carolynn. He placed his hands on my head and positioned me like I had positioned Carolynn. He had me bobbing up and down on him producing waves of apparent ecstasy as he began to pump in rhythm with me. Again, I should have been revolted. But maybe I was a latent homosexual or something. I found myself enjoying sucking on his cock. I was eagerly awaiting his climax so that I could taste his cum. I enjoyed making him happy. I was having fun. I was so absorbed in what I was doing that I was oblivious to anything else. Without warning, a hand went under my dress and started caressing my pantyhosed legs. Someone sat down beside me opposite from Tom and leaned over me. Carolynn whispered to me, "Go girl, he's enjoying every second. You're doing a wonderful job." I hadn't even heard her come into the room. She leaned over me and began to kiss her husband. I couldn't see much, because my face was down, but it was obvious they were French kissing. Tom became aroused even more. He started to tense, and his cum squirted out of the end of his organ directly onto my tongue. He had broken off kissing Carolynn as he began to lose control from his orgasm. He was simply gasping, but Carolynn looked down and gave instructions. "Swallow hard. Keep your lips tight around the shaft. Do a good job. Don't lose a drop." I didn't lose a drop. "Now keep your lips tight around him until he goes flaccid. You should always keep your man tightly in your mouth until he is limp. He feels better if you do that." I kept my mouth around Tom's dick until he put his hands on my head again and said. "Enough." I sat back, exhausted. It had been a lot of work. But things were not over. Carolynn knelt in front of me and pushed the hem of my dress up while putting her hands inside my pantyhose. She pulled them and my red panties down until she uncovered my now swollen member. She was a master of fellatio and began to suck on me until I started moaning. I shouldn't have been surprised at what happened next, but I was. Tom came close and started to French kiss me while Carolynn sucked on my dick. It was too much, I came after a few minutes, and Carolynn held me in her mouth until my excitement was gone. I put my hand on her head and said, "Enough." I was contented, and we were all quiet for a while Tom looked at me and broke the silence. "Well, Barbara, have you had a pleasant evening?" "Yes, uncle, but I'm exhausted." "Good. Then we go home and get some sleep. You and Auntie Carolynn need to fix your makeup first so that you don't look to disheveled when we go past the guard." Carolynn had brought everything. She had me sit in Tom's executive chair while she redid the makeup around my mouth and gave me a fresh coat of lipstick. Tom was taking the original coat of lipstick off his face but had kept some of it on his prick to remind him of me. Carolynn only had to wipe her face and touch up her lipstick a little. We left the office and walked past the guard. He wished us all a "Good night." We thanked him and wished him the same. "Pretty niece you have, Mrs. Kaly," he commented. I took the compliment gracefully and smiled. We got back to the Kaly house late. I was really tired. I went into Alice's room only to find a girl's nightie on my bed. I figured Carolynn wanted me to wear it so I stripped out of my dress. Carolynn stuck her head in before I got out of my panties and reminded me to wash all of the makeup off in the bathroom before I dressed for bed. I walked down the hall with only my red panties on and took a quick shower washing off everything on my face. I returned to Alice's bedroom and put the nightie on. Carolynn reappeared, also dressed for bed. "Well, Edward or Barbara, whichever, do you want to sleep with me or with Thomas tonight? Uhhhhhhhh, don't make a choice. We have an extra king size bed. We'll all sleep in one bed with you in the center. That way, either Tom or I can play with you." Once more, I was surprised. I hadn't expected that they would want to sleep with me also. Carolynn escorted me into the master bedroom. Tom was in a pair of pajama bottoms with no top. I got into bed first and took the middle. Tom was on one side and Carolynn on the other. Carolynn and I were both in nighties and Tom was in his pajama bottoms. Even though I was very tired, I didn't sleep well. I was too excited. When morning broke, Tom and Carolynn had a quick discussion about who had dibs on me. Because Carolynn hadn't climaxed the night before, she had priority. She put her hand in my nightie bottoms and quickly brought me to an erection. There wasn't much foreplay, and I was soon on top of her balling her like I had done so often before. Except this time, Tom was lying next to us watching every move. It was another adrenaline rush, making love in a nightie with my lover's husband examining everything I did. For the rest of the month, I spent a lot of time as Barbara. I would generally go over to my parent's home in the morning to check it out. When Carolynn came home, she and I usually had sex with me as Edward. It took too much effort to dress as Barbara and then reapply my makeup after playing in the sack. I would quickly get dressed as Barbara after our bedtime game, and Carolynn and I would go out together. Often we went to the mall to shop. I accumulated a nice array of panties, slips and other lingerie, usually buying things that Carolynn thought would excite Thomas. It was his money after all. We hit all of the dress shops and shoe shops. For shoes, I had pumps, flats, slings with ankle straps and stylish boots before it was all over. I had dresses and skirts of all shapes and styles but no pants. I enjoyed being a girl. No one ever said a thing at the mall. When Thomas came home in the evening, we would have supper. Barbara would then sit next to him on the living room sofa. One thing would always lead to another, and Barbara would eagerly give him a blow job to relax him. I enjoyed being a girl, and I enjoyed being a girl giving comfort to a man. Well, all good things must come to an end. My parents returned, and I went back home to live in my drab boy clothes. My mother didn't quite understand, however, why I started wearing long pants. Sparky came home for a week before we both left for college. Sparky couldn't understand why I had lost my sense of enjoyment for computer games and just watching girls. Neither one of them knew I had scored with both Sparky's stepmother and his father. All in all, it had been a good summer. I had gone both ways and enjoyed both ways. It was an experience I will never forget.