by: Karen Flynn
I just got home after dropping Colleen at the airport the house was empty. It was the first time that the house had been empty in 17 years. My wife had died two years ago and I had been raising my daughter Colleen alone. She started her last year of high school in two weeks and the remnants of our shopping trip were strewn about the family room. I have to admit she had a very good taste in clothes the skirts, dresses, panties and bras she had chosen were very cute, Expensive but cute. Colleen looked a lot like me tall and skinny, We both had long blond hair I kept mine in a pony tail she kept hers in a tangle. We had had her when I was 17, I am 34.
Her aunt, My late wives sister who also was Colleens namesake had called yesterday. She some how ended up with an extra plane ticket for a teen aged girl to Europe and had offered to take Colleen for two weeks, Perfect. We had just finished her shopping for school. The next 24 hours ending with her getting on the plane had been the most hectic I could remember I was exhausted. Laying back on the couch in the family room I turned on the TV. They had a fashion show for back to school teenage girls watching I realized that Colleen was right on top of the fashion. Picking up a pair of her panties that were laying there next to me I caressed the silken fabric while watching the cute girls on the TV. I thought of my Colleen she was very pretty I looked across to her picture on top of the mantle. Not for the first time I thought that is what I would have looked like if I had been a girl. Caressing the silken panties I picked up the matching bra thinking Colleen needs to grow a little in the chest area. Drifting off I fondled the silken garments thinking back to my teen years when I used to sneak into my older sisters room when she was away and try on her clothes, They were not a very good fit because she was shorter and rounder but the sexual feeling was wonderful. Colleen came along when I was age 17 and I married her mother Susan who frowned on any attempts of mine work crossdressing into our sex life. I buried any thoughts. The thought of Susan brought with it a pang of mourning which brought me back to the present. I found myself laying on the couch in full view in the family room holding my daughters lingerie with a massive erection. I jumped to my feet and thanked god Colleen had not walked in when I realized Colleen would not be home for two weeks, I had the house to myself for the first time in 17 years. Still caressing the panties I got an Idea, I got a very naughty Idea, I got a very naughty, wonderful idea.
I reached up and pulled the rubber band from my shoulder length hair bending over I fluffed it out a little. Looking across to the mirror I looked at Colleen’s picture. I knew we were almost exactly the same size. In the past few months Colleen had been able to wear my jeans and Tee shirts looking at all the cute new dresses and skirts laying around the room I knew exactly what I was going to do. I took the bra and panties I was holding and headed for the bathroom, Colleens bathroom, Stopping first to get my razor. Taking a shower I used her conditioner on my hair and proceeded to shave my face, legs, Chest, arms and Under arms. After I dried myself I looked in the mirror. I had always been a little heavy in the chest area before this moment it had always been a source of embarrassment suddenly it was an asset. I pulled the silken panties up around my swollen cock and managed to finally get the bra on and adjusted. Except for the tent in my panties I looked very feminine apparently Colleen and I had the same bra size. Going into Colleen’s room I looked in her dresser for the first time ever. I was looking for some pantyhose. Much to my surprise I found a garter belt and stockings. Without thinking the implications through I decided to try them on. They fit perfectly much as every thing else had so far. Sitting down at the makeup table I reached up pinching my own nipples. My cock was now so hard that It was coming out of the panties and I had it restrained under the garter belt. Picking up a lip liner pencil I drew a smiley face on the tip of my cock I used the makeup much as I remembered watching Susan use it. I also used the glamour shot picture of Colleen as a model. First I dried my hair with the blow drier fluffing it as much as possible then the Eye liner and shadow, mascara, foundation, blush and lipstick looking in the mirror I could not believe how much like Colleen I looked, What a turn on. Looking in her closet I was surprised to find her shoes were to big for me. I looked through the dresses but I had my heart set on a new one we had bought yesterday. It was black with white dots and a short flared skirt. I almost did not want her to buy it because it made her look to sexy. On my way back to the family room I stopped in my room and found a box of Susan’s shoes in the closet selecting a pair of black pumps I tried them on and they fit perfect, Walking in them out to the family room proved to be difficult finally I got there and selected a short silken slip that fit me like it was made for me and felt so soft and sexy that I almost creamed right then, Next came the dress which fit me better than it had Colleen. Looking at her picture I had a slight bit of remorse when I though of what she might think if she caught me wearing her clothes. Pushing these thoughts aside I walked back to Colleen’s room to see the finished effect in the full length mirror. I was astounded, I was my daughter ! I moved around viewing myself from all angles there was no mistaking it I looked like a teenage girl! What an incredible turn on. This was something I had fantasized about all my life. Pulling up the dress I could see my cock trying to break through the panties and garter. Freeing myself I dropped the dress and slip on to my cock and started to stroke myself through the silken material. In a matter of moments I had reached critical mass and was very careful not to get any on the slip or dress. Afterward I was able to tuck my cock completely back between my legs I was marveling at how feminine that made me look in panties and a garter when I started to get aroused again. Dropping the slip and skirt to cover myself. I remembered Colleen’s Cheerleaders outfit hanging in the laundry room and decided that I may never get another chance to wear one and walked out into the family room. Looking across to the sliding glass doors that go out to the pool. I was horrified to see Colleen’s friend Diane standing there in the open door. I froze and went into shock. Diane looked at me and said "Colleen ?" In a very questioning voice. Still frozen with shock I said nothing. Diane walked into the room towards me. My first impulse was to run but I just stood there. Diane came closer and looked at me very strangely and said "You are not Colleen, Do you know where she is ?" I realized she had no clue who I was.
Diane is a very beautiful girl at 19 years old she is almost 6 foot tall. With long pretty legs, Big brown eye’s and shoulder length nut brown hair She’s very skinny but she has the most incredible cleavage. If she were not my daughters best friend and 15 years younger I would have been all over her. Surprisingly enough I had never seen her with a guy or on a date. Finally realizing there was no way out I said "Colleen went to Europe this morning with her aunt for two weeks." Diane uncomprehendingly stared at this teenage girl who looked just like her best friend but spoke just like her best friends father. Diane just looked me up and down for a few moments. I moved over to the bar and poured myself a shot of Jim Beam which I downed immediately. I then poured another one offering it to Diane. She took it from me and sipped it making a grimace. I poured myself another one which I also downed. Finally I asked "Diane don’t you knock before you come into someone’s house ?" Diane finally downed the shot and said "Is that you Mr. Macky ?" I replied "No its my twin sister." Diane looked even closer at me and said "You look real cute, I never would have known if I had seen you on the street. You look like a slightly older Colleen." Pouring us each another shot I picked mine up to sip it and said "I know I was just." Diane interrupted me and said "You don’t have to explain, My brother wears my clothes all the time but he does not look near as good as you do." She picked up her shot and downed it. I asked her "Will you promise me you won’t tell Colleen ?" She got an evil look in her eye’s and said "Under one condition, You go out on a date with me tonight. You know I have had a crush on you forever." I looked her up and down, She had on black dress very similar to the one I had on, She looked very sexy as usual. I could do much worse things than go out on a date with this very pretty young girl so I said "OK, Let me get changed." Diane smiled a very mischievous smile and said "No I want you to go dressed like that." I replied "No way." Diane responded "Oh come on no one will know you. You look just like a girl and besides if you don’t I will tell Colleen you were wearing her clothes." What could I do ? Diane grabbed me by the hand and started dragging me toward Colleen’s room saying "We need to do something with that hair." Going into Colleen’s bathroom she sat me down and got a spray bottle and some rollers and proceeded to wet some of my hair and put some rollers into it. She said "You have very sexy hair." Turning around she turned back with some scissors I tried to object but she was to quick. She told me "Don’t be nervous I wont cut to much and it will improve your male appearance as well. " After a few minutes of cutting, Combing, Spraying and Blow-drying she started to redo my makeup talking all the while she said "I like what you did with your makeup but I want you to look a little more seductive." Finally she was finished and said "OK now go look in the mirror. The image I saw in the mirror no longer looked as much like Colleen but definitely looked sexy. I would have asked me out. Looking at the two pretty girls in the mirror was a definite turn on. I could not believe one of them was me. I got embarrassed as my skirt tented out in an alarming fashion. Diane looked down and giggled as she said "Oh, You naughty girl." I did not even attempt to stop her as she reached down and started to stroke me through the dress after all if I stopped her she would tell Colleen. Moving around she kissed me full on the mouth I could not resist as I pulled her to me. After a moment I looked over her shoulder and the image in the mirror of two sexy girls locked in a passionate kiss was to much and the feeling of these wonderful clothes against me was incredible as I pressed my fully erect cock against her. Finally breaking the kiss we both looked into each others eye’s and knew what was to happen next. We walked through the door into the bed room I looked into the dresser mirror as she walked up behind me she reached around cupping both of my breasts she pinched my nipples as she nuzzled my neck she whispered into my ear "I don’t think you know that I like girls, You will be the first man." Looking into the mirror I said "I don’t currently look to much like a man." Diane replied "I know and that has me incredibly turned on." As she slid one hand down again gripping my cock though the silken garments. Not really wanting to know I asked "Have you and Colleen." She again interrupted me and said with a sly smile "Have we had sex, Yes. Are we lovers, No. She prefers men." Somehow this relieved me and turned me on at the same time. Diane reached under my dress finding the garter belt she said "I gave this to Colleen." Pulling down my panties she grabbed hold of my monumental erection. Not quite believing that I was standing here dressed up in Colleen’s clothes about to make love to her best friend I reached down and grabbed hold of the hem of her dress and pulled it up over her head. She was wearing the black version of the white that I was wearing, Black lacy bra, panties, Garter belt and shear stockings. The big difference was her fabulous tits. I stood there looking at her for a few seconds finally reaching up to cup her breasts through the silken bra pinching her nipples. Diane responded by pulling my dress up over my head. After looking me over she said "You look just like your daughter except for this." As she reached down and grabbed my cock "But these are perfect." As she reached up cupping my tits and squeezing my nipples. I pulled her to me rubbing our tits together I kissed her while I unhooked her bra. As I moved back I reached up caressing her tits that I had fantasized about for so long. Reaching down she dropped her own panties about her ankles. Moving forward I pushed her to a sitting position on the bed she reached up and grabbed my cock with both of her hands she looked straight at it and started to giggle when she saw the smiley face I drawn there earlier. Leaning forward she kissed me on the smiley face. Looking up she said "I have never touched a mans cock before am I doing all right ?" I said "Perfect" As I leaned down and kissed her pushing her backwards I kissed her on the breasts and started to nibble at both of her nipples finally kissing my way down I kissed and lightly started to lick at her button. She gasped and said "Oh god, That feels good." I moved down and circled her pussy with my tongue finally going back to her button I gave her a tongue lashing she will not soon forget. When she grabbed me by the hair and started grinding my face into her pussy I figured she was ready. Moving back up stopping to nibble her nipples again. I stopped when we were face to face. Kissing her deeply I moved in until just the very tip of my cock was touching her steaming pussy. She tried to push up but I kept just the tip touching for a while. Slowly I pushed ahead getting a gasp out of her until just the tip was inside. Looking into her eyes I asked if it hurt. She replied "Yes, I mean no." Pushing slowly forward until all 9 inches were buried in the tightest pussy I had ever fucked. Diane’s eye’s were glazed over as I started stroking slowly in and out. Kissing me she gasped "This is wonderful." Slowly I picked up speed I could feel the eruption building but fought to hold on. Diane reached around me and unclipped my bra. The incredible feeling as my suddenly naked nipples rubbed against hers was awesome. Suddenly she bucked up into me with enough force that she almost threw me off the bed. Her already tight pussy gripped my cock in a death grip pushing me over the edge. I held on to her as she jumped like she was possessed. My cock exploded sending waves of ecstasy pulsing through out me. I must have pumped at least a gallon of ecstasy into her. After what seemed like hours of blinding passion. I lay on top of her in the fading afterglow. Rolling to the side I looked up into a face of pleasure. She said "I can’t believe I have been missing that all this time, Why didn’t someone tell me ?" I replied "Honey, I am glad you waited because that was the best." Looking me back in the eye’s she said "There is plenty more where that came from." Getting up went to head to the bathroom when she picked up the phone and dialed a number. Stopping I watched here as someone answered the other end of the line she said "Hello, Ma, Yes,, OK,,, I will be spending the night at Colleen’s.,,,, OK, By." Then she smiled at me and came over and kissed me and said "I think we need to get dressed, you have a date tonight."
If you liked this story or didn't like this story Email me at SONOFAK@AOL.COM and let me know. The only way I can get better at writing these stories is if you let me know what you like or don't like or maybe would have done differently Or which parts really turned you on. Thank you for reading my story Karen Flynn.
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