This is my cross dressing story. It is basically true. It happened over 40 years ago. I am a little fuzzy on the timeline. So I wrote it as I remembered it. I probably went into to much detail but as I was writing more and more detail kept coming back to me.
I don't know exactly when I started wearing female underwear. I do remember when I was twelve or so and I had just learned the wonders of masturbation. I found a pair of my older sisters nylon panties in the clothes hamper and was intrigued by their feel and tried them on. They felt wonderful against my bare skin. I got an erection and masturbated. I was hooked from then on. I also loved the female and perfume smell of the cotton crotch panel. I would put the panties over my head and smell the crotch before I jacked off. It wasn't long before I graduated to more than just panties I tried on my mother's dresses with silk slip and nylon stockings. Her dresses fit me but her panties were to big so I stuck with my sister's panties. I found myself unable to stop this obsession. I would put on my mothers green satin party dress with slip, garter belt and stockings and lacy panties. I would put my cock between my legs. Then I would stand in front a full-length mirror and slowly raise the dress revealing my stocking clad legs then my bare thighs with the garter belt and finally my panties. I fantasized that I was looking up another woman's dress. This would turn me on and I would masturbate and cum in my sisters panties. I kept up this behavior throughout my teen years.
When I was thirteen my grandmother died and I helped my mother dispose of my grandmother's clothes. I managed to save several under garments from the trash. I now had my own girdle several pairs of nylons, slips and several pairs of nylon panties. Unfortunately my grandmother mainly wore white boxer panties. I preferred briefs. But I did salvage one pair of pink lace briefs. They were so pretty; I couldn't imagine my grandmother wearing them. Soft pink with lace all over the front and shear pink nylon in the back. They had a dark pink rosette and bow in the middle at the waist. I felt so sexy when I put them on. I would stand in front of the mirror and model them. I loved how I could see the crack of my ass through the sheer back. I have reddish blond pubic hair so I could barely see my pubes through the front lace. I would use an eyebrow pencil to darken my pubic hair and with my cock tucked between my legs it would look like a woman's pubic area through the lace. This would really turn me on and I would quickly cum. The girdle was an open legged one with garters so it fit right in with my fantasy of looking up a woman's dress.
When I was fourteen I moved in with my Aunt and finally had my own room. I never seemed to want a bra although I had tried one of my sisters on several occasions. My Aunts clothes fit me so I had a whole new treasure trove of feminine attire. We lived in the suburbs and only had one house next to ours with a field on the other side. My room was in the basement and I could go out through the garage into the field next to our place virtually undetected. The laundry was also in the basement so my Aunts underwear was always handy. At night, after I went to bed, I dressed up in my favorite sexy feminine attire and would sneak out into the field and romp about in my sexy underwear. That is in the summertime. Winter my dress up was an indoor activity.
When I was fifteen our neighbors wife passed away. Within a year our neighbor remarried. She was a beautiful full figured woman and I liked her immediately. One night I was looking out our basement window toward her house and I noticed her bedroom window shades were open. I stared for a few moments at the window and to my amazement she passed by naked. My cock came instantly to attention. In a few moments she reappeared in a lacy white robe that was open in the front so I got to see her large tits with dark areola. From my angle I could not see her crotch, but the view was great. Next, her husband came up from behind her and reached around and grabbed her beautiful tits. She stood there in the window while her fondled her tits. Then she turned around and her head went down nearly out of sight. I could see him standing there bare chested as her head bobbed up and down. Although I couldn't see her taking his cock in her mouth it was obvious she was giving him a blowjob. The only window on that side of our house was my small basement window so I am sure our neighbors felt secure leaving their bedroom window curtains open.
From then on, I would dress up in my feminine attire nearly every night and watch the window. I was not treated to a sex show every night but on occasion I got to see her beautiful tits and negligee. I got some really great close-ups of those beautiful titties using a pair of binoculars. I tried a couple of times to get a better view by going outside and looking in their window from the ground but we had a backyard light that made it very risky to get to that side of our house especially dressed in panties and a slip.
Later that summer I started doing odd jobs for her almost everyday. She liked me and enjoyed my help. I found out she did laundry on Monday's like most people, so I took advantage of that. In the middle of the week I would go through the dirty laundry and find her panties. She wore sexy panties all colors with lace and even some bikini's and they fit me perfectly. I would get a pair and go to the bathroom and put them on and wear them home. That night I would masturbate wearing her panties while watching the window for her to walk by. I could smell and taste her pussy and perfume in the crotch of her panties. She must have washed her lacy nightgowns by hand because they never seemed to show up in the clothes hamper. I would wear the panties back the next day and put them back in the hamper.
Late in the summer she got a job. She worked for the Red Cross four hours in the afternoon. She hired me to take care of her German Shepherd while she was at work. What an opportunity, I had free reign of her house in the afternoons and I could almost stay as long as I wanted without arousing suspicion from my aunt.
The first day I went straight to her bedroom and looked for her underwear drawer. She had one drawer in the chest of drawers that was all underwear, panties, bras, garterbelt and girdles. In another drawer were her nightgowns and slips. I found stockings in another. Her dresses and skirts were hung neatly in the closet. There was a problem, all her panties and bras were folded in rows. Everything was carefully placed in the drawer. To get the items out and back in the drawer exactly as I found them would take a great deal of care. Also, I knew she was very meticulous and I dare not even leave so much as a pubic hair on her precious things. This was going to take some time and thought for me to realize my goal of putting on an entire outfit of hers. That day I used her soiled panties out of the clothes hamper to masturbate with. I decided to dress up in an entire ensemble of black. She had a black dress and slip. Black panties, girdle, bra and stockings. I did not have any black female clothing of my own so black was exciting to me. I got a hard-on just thinking about it.
The next day I was ready to fulfill my fantasy. I started by carefully selecting the things I was going to wear. I removed them from the drawers very carefully noting their exact location and how they were folded. I got a pair of lacy black panties. I removed her black open-legged girdle. I got a pair of black stockings and a black half-slip. I selected a black bra and noted that it was an underwire bra size 38C. I went to her closet and took a black dress off the hanger. I carefully wrapped some toilet paper around my cock and tucked it between my legs. I put on the panties and pulled on the girdle. Next I put on the stockings connecting them to the garters. I put on the half-slip. I had to find something to stuff the bra with also it was just slightly too large. I decided to use some of her panties from the dirty clothes hamper to stuff the bra. That idea worked out fine. The dress was a little tight around the waist but since we were about the same height and build. It fit in the shoulders and was the right length. With a little urging I was able to get it zipped up and went in the hallway to look at my handy work. I was standing in front of the hall mirror admiring myself fully dressed in black. My cock was hardening between my legs. I thought I looked good as a woman. All of a sudden, I heard a voice. God she was home and standing in the kitchen door. I spun around as she was yelling what are you doing young man get out of my clothes. I quickly ran down the hall and went into her bedroom and started to unzip the dress and pull it over my head. I was having a devil of a time trying to get the dress off. I was crying and sobbing how sorry I was while struggling with the dress. She came in the room and told me to stop or I would tear the dress. She came over to me and told me to stand still and she unzipped the dress and helped me get it off. I was still sobbing how sorry I was as she undid the bra and reached around me and took it off. I slumped down on the bed facing her. I just sat there in her half slip and stockings. My hard-on was long gone. She seamed to calm down as she sat on the bed next to me. She put her arm around me and asked why I had her clothes on. I told her everything. How I liked the feel of nylon and that I stared by wearing my sister's panties. I even told her that it sexually excited me. When I finished my confession we just sat there. Finally she got up and said well I guess theirs no harm and you did look good in that dress. She told me to go ahead and finish getting undressed. I stood up and started to remove the slip. I was surprised she was still standing there. I thought she would leave the room but she was just standing there watching. I stopped with the slip down to my ankles and looked up at her. She said for me to continue. So I did. I folded the slip and laid it on the bed. I sat back down and undid the garters on the girdle and removed the stockings. My hard-on was back. I was embarrassed and I knew it would show as soon I pulled down the girdle. I looked at her again and she motioned for me to continue. I stood up and pulled down the girdle as I did my panties were coming with it I stopped and pulled up the panties and finished removing the girdle. My cock ballooned out in front of the panties. I must have hesitated again because she told me to go on. I pulled off the panties and stood there fully naked in front of her with my cock sticking out in front of me. She said I have been missing pairs of my panties once in a while. Do you know anything about that? Have you been taking them home with you? I said yes out of the dirty clothes I would wear them home and bring them back the next day. I didn't think you would notice.
We both stood there for a moment and to my surprise she started to undress. She was wearing a skirt and sweater. She unzipped the skirt and stepped out of it as she pulled the sweater over her head. She had on a lacy full slip. She also pulled it over her head. Then she removed her bra and exposed those beautiful tits. She was just wearing a garter belt, pink panties and stockings. She picked up her skirt and along with the sweater and slip she folded them and laid them in a chair. She looked at me and asked if I liked her breasts. I didn't answer I just stood there with my mouth open. Come here and help me finish undressing. I stumbled over to her and as I started to undo her garters my cock rubbed against her thigh. She was standing with her legs spread and I knelt down as I removed her stockings my face was right by her pussy. I reached around her waist and undid her garter belt. Again my face was inches from her crotch. I could smell her perfume. My cock was huge it had never been this big. It was at least six inches. I reached for the waistband on her panties and started to pull them down. Her dark bush came into view as I pulled her panties down to the floor. With her panties around her ankles she rubbed her pussy and asked if I had ever seen a woman naked. I lied and said no and she took my hand and led me to the bed. She lay back on the bedspread and told me to feel her vagina. She spread her legs and I saw my first pussy through a mat of coal black hair. I took my hand and started to feel her cunt. She was very wet that surprised me. I let my fingers open her hole and they slid right in. I put my thumb on what I thought was her clit. She started to squirm as I fingered her wet hole. She was rubbing her large nipples then she asked me to suck on her tits. I climbed up her and kept my hand on her cunt while I put my mouth on her right tit and started to lick and suck on her nipple. She reached down and grabbed my cock and started to rub on it. Almost instantly I shot my cum all over her legs and bedspread. I stopped what I was doing and started to apologize. She said not to worry and started to lick my cum off of her hand. The next thing I knew she had my cock in her mouth sucking the last bit of cum out of me. Somehow I managed to keep my hand on her cunt. I now had four fingers deep inside her hot hole. She squeezed her legs together and said now I had to help her by sucking on her vagina. She straddled my head and lowered her pussy down to my mouth. I started to lick and suck on her cunt. She tasted just like her cotton crotch panels on her panties except there was more. Her pussy was really wet as she ground it against my mouth. I could taste her cum as I swallowed tons of it as it poured out of her hole. This was amazing; here I was a sixteen-year-old teenager eating out a beautiful woman. I had my tongue as far in her hole as I could and she was screaming as she had an orgasm. My face was flooded with her hot cum. She rolled over on the bed and lay there with her eyes closed. I reached out and felt her tits.
After a few moments she said that we would have to keep this as our secret. She wouldn't tell my aunt about my dressing habits and I would not tell about our lovemaking. She got up on an elbow and looked at me for a second then said I really did look good as a girl and that she would enjoy helping me play that role. She would dress me and make me up and since she did not have children I would be like her daughter. I thought this was strange but as she said it she started to gently rub my cock into a full hard-on and I immediately agreed. She said it was time I lost my virginity. She spread her legs and motioned me on top of her. As I mounted her she led my cock into her pussy. God what a feeling as my cock slipped fully into her hole. I thought her mouth on my cock was amazing but her warm moist pussy felt even better. I started to move in and out as she guided me by grabbing my ass with both hands. I don't know how long I lasted but I know when I came that time it felt wonderful. I could feel my cum injecting into her body. I think she came with me because we both stopped moving and just lay there. She grabbed my face and we kissed deeply. I slowly got up relishing the great feeling as my cock pulled out of her. She got up and handed me the pair of black lace panties that I had worn earlier and said go ahead and wear these home today you've already got them soiled. I will see you tomorrow and start your feminine training. She put on a robe as I found my pants and shirt and dressed. As I was leaving she pulled me to her and kissed me again. I went home in a daze.
That night I jacked-off at least four times. I fell asleep anticipating the next day. I went over to her house the next day at my usual time and found a note on the kitchen table. She told me to be wearing the clothes she laid out in the bedroom when she got home that afternoon. I went quickly to the bedroom and found an outfit on the bed. It looked like the same outfit that she had on yesterday. A pleated skirt with sweater, lacy slip, bra, garter belt, stockings, and pink panties. I couldn't wait to try them on. I put on the garter belt then the stockings and panties. When I started to put on the bra I noticed it was a different size than her 38C. It was a 36B. It fit a lot better and it only took a small hand full of tissue to fill up the lacy cups. I'll bet she went out last evening and bought this bra for her new daughter. I put on the slip. It was satin and I never felt anything so sensuous on my bare skin. I went out to the full-length mirror in the hall and admired myself in her pretty slip. I rubbed it up and down my body. I finished putting on the sweater and skirt again; I admired myself in the mirror. It was time to let the dog out for a run. I decided to take a chance and go outside with the dog dressed as a girl. Their back yard is fenced and the only person that would be looking in the yard would be my aunt and I knew she was taking her nap at this time. She never missed a nap. So I took the chance and the dog and I went out in the backyard.
It was a windy day and the first thing I noticed was how good it felt as the cool breeze rushed up my skirt onto my bare thighs. I romped around in my feminine attire like the dog. I twirled the full skirt and took my panties off so I could feel the air on my cock and balls. I went back in the house and jacked off in front of the mirror.
When she got home she looked me over and said I looked nice but I needed to learn to put on make-up if I wanted to be a real girl. She started to refer to me as her little girl. She called me Susie when I was in feminine attire and Billy (my real name) when I was a boy. That made me somewhat uncomfortable but I knew I would get to play with her magnificent body if I played along.
The next couple of weeks she taught me to put on make-up and I got to dress-up in all kinds of feminine attire. She gave me a drawer in the spare room dresser to keep my girly stuff. I loved the baby-doll pajamas and the lacy nightgowns. I started to take them home and wear them to bed at night. She made me some breast forms out of a satin material filled with something I'm not sure what but they worked very well. She also bought me a wig. It was a short blond wig not quite to my shoulders cut in a page boy style. We both wore size 8 1/2 shoes but hers really didn't fit so she bought me a pair of flats that I could wear. As for the make-up I wasn't a very good student but I finally got the hang of it. I was amazed how just a little eye and lip make-up really transformed me into a pretty good-looking girl. She said when I was made up I looked older at least eighteen.
She said I had a great female body from the waist down. She said my butt was perfect. Most women would give their right arm for a butt as pretty as mine. It was round and firm. Not flat like hers. I didn't understand what she meant but I took the compliment and enjoyed it. She also said my legs were almost as perfect. That I did understand. When I looked at my shapely legs in the mirror with stockings on, I knew they looked good. She also taught me about the fashion accessories purses, scarves, jewelry, perfume and all that kind of stuff. It was so much easier to be a boy. She taught me to walk and sit like a girl. I caught on to that easily. I think I was born a little more feminine than masculine. She said I had a natural "swish" when I walked and all I needed to do was to accentuate it a little.
The biggest problem with my transformation was my hands. I worked outdoors a lot so my hands were rough and my nails were terrible. She told me to use hand cream all the time. I had to always wear gloves when I worked. She also had me use the cream with gloves at night. This regimen seemed to work so after a couple of weeks my hands and nails were better.
I also got trained on the female anatomy. One afternoon she got on the bed with a mirror and spread her pussy open and showed me all the parts. The inner and outer labia, her clit and where she peed from. I had to name each part as I kissed it. She said all girls need to know everything about their vagina. Right then I wished I had a vagina and tits but I wanted to keep my cock too. She taught me how to pee like a girl. To sit on the toilet and wipe myself. She said all girls needed to keep their vaginas clean. So while dressed as a girl I had to set down to pee and wipe my cock.
When we were making love she showed me several positions. She taught me to eat her out so she got the most pleasure from it. She liked me to use my tongue on her asshole while I ate her out. When she got ready to cum I would stick two fingers in her ass and she would cum a ton. She used that same technique on me when she sucked me and I can't believe how good it felt.
It felt like I was dealing with four different people. When she was teaching me about female dressing she talked to me as her teenage daughter. When we were making love I was her masculine lover and she had a wild look in her eye. When we were around other people I was just the kid next door and when she taught me the female anatomy it was like I was a little girl. I could see her personality transformations happen right in front of me but I don't think she was even aware she changed.
The last week of summer vacation was here and Janet's job was over. Oh! Have I mentioned her name? Well she is Janet and her husband is Jim. At the end of summer vacation my aunt and uncle had an opportunity for a two-week vacation to New York City to visit some friends. Since, I had to start school in a week it was decided that I would stay at home under the watchful eye of Janet and Jim. I would sleep at home and eat at their house (hooray). I think Janet was as excited about this arrangement as I was. I also got a job mowing about five hours each morning. So by a little after noon I was free.
Janet decided that it was time I went out as her girl. This scared me half to death but it also excited me. She said we would go to a shopping center in her old hometown about fifty miles away. If I could finish early on Thursday we could get there in time for a late lunch and we could shop for clothing. I got my mowing done by ten thirty and went to her house to shower and prepare for my going out party. When I got in the shower she came in the bathroom and said I needed to shave real close. I could use her razor and we needed to do something about my leg hair. I protested. I said I could not shave my legs I was still wearing shorts and I wouldn't be able to go to school with shaved legs. She said she understood since my hair was blond maybe she could use her hair clippers and just remove the long hair. She assured me nobody would notice. I finished showering and shaved my face under her watchful eye then I sat on the toilet while she used her clippers to remove the hair from my legs. I must admit she did a good job. I still had leg hair but from a distance it would not be noticeable through my stockings. She had chosen a favorite outfit of mine for me to wear. A burgundy pleated skirt with a pale pink sweater. I was wearing all pink underneath. I got admonished again about putting my make-up on too heavy. She said I must have some French whore in my background because I always applied too much. She gave me a shoulder length purse to carry. Since I had not carried a purse before she thought there would be less chance of me losing a shoulder bag. Instead of getting in the car in the garage she had left it outside in the driveway. So I had to walk outside and get in the car. This was my first real exposure to the outside world dressed as a young girl. I found it exhilarating.
The drive to her hometown was uneventful she talked about the stores where we would be shopping and where we would have lunch. She could tell that I was getting anxious the closer we got to our destination. She assured me I would not be found out and that I looked lovely. She was sure my feminine actions would not give me away. Relax and enjoy. Just remember we could share our experiences in her bed when I was acting more like a man. I liked that comment and it did make me feel more at ease.
We arrived at something like today's strip mall. There was a major department store with several side shops and an Italian restaurant with outdoor seating. She said we would eat at that restaurant. We parked in the middle. With some trepidation I got out of the car and followed Janet to the restaurant. It was a nice day so we were seated outside. After we ordered she got up and said come on honey lets got to the restroom. Uh oh, I don't know why but I hadn't anticipated that even though I did need to go. I would have to use the woman's restroom. I followed her into the restaurant and to the door marked woman. When we went in there was nobody inside. She told me to use a stall and don't worry no one was going to barge in and see me peeing with a penis. Just pull your girdle and panties down and sit on the toilet. Use some toilet paper to wipe yourself. I told her I remembered how she taught me. When I grabbed my cock it immediately started to get hard. I had to focus my attention on something else to be able to pee. When I came out of the stall two elderly women came in and they just smiled and went about their business. Janet was at the mirror fixing her hair so I followed suit.
We had a good lunch and I was getting used to my feminine role. She said we would shop for dresses. Her and I and that it would be fun trying them on. Oh god another thing I hadn't anticipated. Trying on meant I would have to undress in some fashion. I wasn't sure what it would be like. We went to the department store and to woman's fashions. She started to look at dresses and told me to do the same. She was a size twelve and her dresses were a little tight on me so she told me to go to the size fourteen rack and look for something nice. I watched as she selected a couple of dresses and went toward the dressing room to try them on. All of a sudden a sales lady came up to me and said the dress I had in my hand would look great on me would I like to try it on. I hadn't talked to anyone except Janet dressed as a girl so I hadn't tried to change my voice. This is one area Janet hadn't brought up in my training. Janet wasn't here so I started to panic then I decided to give it a try and I answered the sales lady just raising my voice a little. No thank you. The sales lady was persistent and she selected another dress and held it up to me and said this one would also look great. I decided to go it alone. I took the other dress and with my selection went toward the fitting rooms. The sales lady was following me and said something that sounded like "here I'll help you". I said no thanks in my high voice. I just couldn't imagine her coming into the changing room with me. What did she mean by helping me? Did she come in the room with me and watch me undress? God! Where was Janet? I was lost and scared. Just as I got to the opening to the changing rooms I saw Janet coming out in a beautiful dress. I stopped to admire her. She saw my worried look and sensed my nervousness. She said honey what do you think and modeled the dress for me. This seemed to sidetrack the sales lady that was following me to my relief. I told her she looked beautiful and she took my hand and led me back toward the dress racks. I think I'll get this one she said let me see what you have. I held up both dresses and she nodded her approval. Go ahead and try the blue dress while I change out of this dress. I asked in a whisper what do I do. She said don't worry there are curtained rooms nobody will look.
Relieved I again headed toward the dressing rooms. I went in and saw a row of curtained cubicles. Janet went into one and I went past her to the first open curtain. I went in and closed the curtain tight. The dress was a short sleeve blue print with a full skirt. I tried it on and it fit perfect. I heard Janet outside my dressing room and she asked me to come out so she could see. I opened the curtain and stepped out cautiously. She said turn around and yes that will do nicely but let's try on the purple one. She had it in her hand and handed it to me. I went back in the room and removed the first dress as I was standing there in my half slip and bra. I felt my cock get hard. Janet was right. I would remember these experiences later and jack-off furiously. I put on the purple one and confidently went out of the changing area to model the dress for Janet. She was standing there and motioned for me to look in the mirror. I spun around and looked in the mirror. I was sold I looked beautiful in this dress. I said I wanted this one and she said go change and we will get it.
When I came out of the changing area and handed the purple dress to Janet she said this dress needs a petticoat. I wasn't sure what that meant until we went to the foundation department and she selected a white petticoat. Then I knew what she meant. Wow I couldn't wait to get home and try on my new dress with the petticoat. She went to the sales counter and paid for it all. We walked out of the store and I know I had a little more swish in my walk.
Janet suggested we get a cup of coffee before we headed home. We went back to the place we ate lunch and sat a table and ordered coffee. After a while Janet left the table to go to the restroom. While she was gone two good-looking boys came by. They looked to be about eighteen and were looking at me. I felt very self-conscious. They slowed down and kept staring. I finally smiled at them not knowing what else to do. The next thing I know they were coming over to my table. What do I do now? They came up to the table and asked me something. I wasn't sure what they said. I was getting panicky again. One guy sat down next to me and asked my name. I mumbled something and suddenly I felt his hand on my knee. Oh my god he was going to feel me up. Just as suddenly Janet returned and the boys got up and she asked them something. Again I wasn't hearing to well. As the boys hurried away Janet said let's go so I hurriedly got to my feet and almost ran to the car.
When we got in the car I started to say something but before I could she started on me. Why you little slut. What were you doing flirting with those boys? I told you to be careful with boys. You especially should know they are all on the make. I saw the one that sat down next to you had his hand up your skirt. Did you let him get a good feel? I was shocked. I stammered I didn't' mean to flirt. I just smiled and they came over. I'm sorry. She saw I was almost in tears. She said there now it's all right. I know you didn't mean it but when you are a young girl you have to be real careful. You know those boys just wanted to get your panties off. I said I know I was relieved and she started the car and we left the shopping center.
On the way home she asked me how many times I had a hard-on today. I said many times. Once in the ladies room and again in the changing room. I also got a little excited when that guy put his hand on my knee. Oh and when I looked in the mirror with my new dress on. How about now she asked? I said yes so she asked me to masturbate for her on the way home. We were on a country single lane road. I pulled up my skirt and slip and pulled off my girdle and panties. My cock was rock hard. I started to jack off. She told me she was getting real wet watching me rub myself. In a few minutes I was ready to cum and reached for a tissue. She told me to cum in my hand not in the tissue and let her taste my cum. So I shot my load in my left hand and held it by her mouth and she licked it while she drove. Then she told me to taste it myself. So I put my hand by my mouth and sucked up the rest of my cum. She said it tasted better coming straight out of a penis. I cleaned myself off and put my panties back on and we drove on home.
As soon as we got home she started undressing almost before we got in the door. She said she needed me right away and we made love in the living room on the carpet. After we finished I changed back into a boy and she started dinner. Jim would be home from work soon so I didn't have time to try on my new dress.
That night I almost wore my cock out jacking off. I had a mowing job that Friday. When I got home and went to see Janet she sat me down for a serious talk. Jim knows everything. I told him about your female dressing and our lovemaking. I was shocked. She said he understands and doesn't mind. He is happy that I have someone to treat like the daughter I have always wanted. He wants to meet Susie. He wants to see you dressed as my girl. I told him that after dinner tonight you would dress up and we would give him a special evening. I was still shocked. Even though she said he understood I said what about our lovemaking. Oh don't worry I made love to other men before I married Jim and he understands my desires. You'll see he is not mad at you. Well ok if you say so but I was still nervous. She said I could wear my new dress and petticoat it would be a very special evening. At dinner Jim didn't let on he knew anything.
After dinner Janet and I went to her room and started preparing for the evening. I had already taken a shower earlier. She had my outfit laid out on the bed. It was my new dress and petticoat along with a new pink lacy matching bra and garter belt. She had a new pair of pink panties. They were not briefs but tap panties with lace scallops at the leg openings They were very pretty but I said what about my penis sticking out. She said not to worry my petticoat would hide any bulges. I got undressed and put on the bra and panties. She gave me a pair of white stockings and I put on the garter belt and stockings and we both admired how pretty I looked. I had a huge hard on as I sat down at her vanity. She painted my nails with a purple polish that matched my dress. Then she helped me apply my makeup. She said when we finished I was to wait in the spare room until she called me and then go into the family room where she and Jim would be waiting. I put on the petticoat and my dress. It felt great with all that lace around my legs. I put on my wig and she put a ribbon in my hair. She gave me a silver necklace and earrings to wear. When we finished she declared I was the prettiest girl she had ever seen. I must admit the dress with the petticoat and all the trimmings did make me look good. Janet was right my cock didn't show. I still tried to keep it tucked between my legs. I went into the spare room to wait her call. I was very nervous but the glass of wine I had with dinner helped me relax a little. They usually had wine with dinner and they let me have a glass. It was normally watered down for me but tonight it wasn't. So I had a little glow on.
Finally, Janet called and I went into the family room. She and Jim we setting on the couch. He had on his robe and she wore a white peignoir. When I entered the room Jim's eyes lit up and he said my god she is stunning. Now they both were referring to me as a girl. Oh well I felt like one then. Janet told me to spin around to show off the dress. She said you should have seen her yesterday. I just left her for a minute and she had two boys flirting with her. One even had his hand up her skirt. I protested that he only had his hand on my knee. Jim said that I had better watch out. Some boys might not like what they find up my skirt. Janet laughed and told me to take off my dress she wanted Jim to see my pretty underwear. I just stood there with my mouth open. She wanted me to undress in front of Jim. Come on sweetie she said as she got up to help me. We girls are going to please our man this evening. I was in a daze but what ever she wanted I was bound to comply. She helped me take off the dress and the petticoat. Jim sat there watching as I stood there in my underwear. Doesn't she look sexy in pink she asked Jim? He agreed. My cock started to harden and the tap panties didn't hold it in so it stuck out in front of my panties.
Janet went over to Jim and sat down in front of him on the floor and asked me to join her. I went over and sat down beside her facing Jim. She opened his robe and to my surprise he was naked underneath. Ooh look what I found as she reached out and picked up his stiffening cock. I was mesmerized by her actions and watched as she got him hard. He had a skinny cock that was longer than mine but not much. His balls were huge. I couldn't get over how big they were. She took my hand and put it on his cock. She told him I liked cum and that yesterday I ate my own in the car. She asked me to help her suck him off. I was overwhelmed but I said all right and we both put our mouths on him. I kissed the head as she encouraged me to take it in my mouth. I remember when I did I thought that this wasn't too bad and started to suck him off. She was rubbing his balls and whispering in my ear how good I was doing. He was moaning and rubbing my head. I don't know how long I sucked on him but soon he was ready to cum. Janet sensed this and told me to get ready for him to cum in my mouth. Don't worry she said it will be all right. He convulsed and shot his load in my mouth. Most of it went right down my throat but I couldn't hold it all and some leaked out the side of my mouth. She helped me clean up the rest of his cum and suck the remaining out of his cock. He said I was an excellent cocksucker. Janet said I knew she would be.
Janet got up and removed her pengoir and told me to get naked too. I took off the rest of my underwear and Janet told Jim she was going to suck me off. I lay back on the floor and she started to suck on me Jim got down on the floor with us and watched closely as she expertly sucked me off. She sucked me dry then asked Jim to fuck her. I watched as he mounted her. She put her legs around his neck and he started to pump her pussy. The whole time he was on her she was shouting fuck me, fuck me, fuck my pussy hard. I watched as his cock went in and out of her beautiful cunt. She had always called her cunt a vagina and my cock a penis before tonight. Now she was using all the vulgarities she could. After what seemed a long time he finally came in her. He got up and she asked him to get us some wine. She lay there glistening with sweat and as she spread her legs open asked me to look at her pussy. She wanted me to see what a woman's pussy looked like after it had been fucked. I positioned myself between her legs and looked at her cunt. It was wide open and his cum was oozing out of the hole. I told her how beautiful it looked and started to clean off his cum with a tissue. She said no use your tongue. I put my head down between her legs and sucked her pussy until I got all the cum mixture out of her I could get. She had another orgasm while I was eating her.
Jim came back with the wine and when he saw me sucking Janet's pussy he said to Janet boy she does like cum doesn't she. We sat around naked and drank a glass of wine. Janet said she wanted Jim to fuck me in my pretty ass. Before I could protest she said don't worry sweetie he will be gentle. Your ass will be like your pussy and he will take your virginity. She poured me a little more wine, which I quickly downed. I reluctantly said okay and asked what to do next. She told me to get on my hands and knees on the floor stick my ass up in the air and Jim would get me from behind. I got on the floor. I could see Jim's cock getting hard. Janet got on the floor in front of me and handed Jim a tube of K-Y Jelly. Jim said she does have a pretty ass as he rubbed it and applied a finger full of jelly to my hole. Janet said okay sweetie he going to enter you now. It will hurt at first but the pain will pass. I felt him pressing his cock against my asshole. As he penetrated me it burned like a hot poker and I winced. Janet saw my discomfort and reassured me that the pain would be over soon. I felt his cock penetrate deeper. It made me feel full. The pain was easing as I felt his balls hit the back of my legs. Janet said he's in he's all the way in. He started to fuck me. Janet was really excited she was encouraging Jim to move faster. I noticed my cock was hard and Janet had her hand in her cunt finger fucking herself furiously. I think I saw her whole hand disappear in her cunt. Jim 's pace slowed and Janet reached under me and grabbed my cock and started jacking me off. She said he's going to cum. you're going to feel it going in you. She said all girls like to feel a man cumming inside them. About then he shoved his cock in me as far as he could I heard him grunt and I felt his cum spurt inside me. At the same time I shot a load of cum in Janet's hand. Jim stayed in me until he had finished cumming. When he pulled his cock out I heard a plop as it come out of my hole. Janet was smiling at me and she said their honey now you have had a man cum in you just like a real girl. She grabbed some tissues and stuck them in my asshole as I shakily got up. I excused myself and went to the bathroom.
When I sat down on the toilet to pee I felt more cum pour out of my wide-open asshole. When I went back to the family room they both had on their robes. Janet told me to go put on a nightgown and come back and set with them. I put on my favorite baby doll nightie and returned to the family room they were setting on the couch. She was curled up beside him and he had his arm around her. She motioned me over to them and I joined them on the couch. I sat next to him and he put his other arm around me and held me close. I drank another glass of wine and by now I was feeling good although my asshole was very sore. Jim said we were going up to the camp tomorrow. They had a small cabin on a lake nearby. Jim had a boat and I had gone there with them many times. Janet said I could go as Susie. I said all right. She said I could wear her yellow top and shorts. She reached in Jim's robe and started to fondle Jim's cock. The next thing I knew we were sucking him off again. She got most of his cum this time. After we finished on Jim she let me fuck her with Jim watching. Of course I had to suck my cum out of her pussy afterward. I was tired so I said I was going to bed. She kissed me and told me I did very well.
When I got in bed I could not go to sleep. I was worried that I had become a homosexual. After all I had just sucked Jim's cock twice and he had fucked me in the ass. Then it dawned on me I was BI-sexual. I loved fucking Janet more than anything and the sex with Jim was all right too. This eased my mind and I went to sleep.
The next morning my ass was still sore as I put on Janet's yellow knit top and shorts. I had on a white bra and a white control brief panty. We drove to the lake. Janet or Jim neither one mentioned our sexcapade from the night before. The panty was uncomfortable but it held my cock between my legs. I had to wear it to keep the front of my shorts flat and feminine looking.
When we got to the cabin Jim started some clean up chores he needed to do. Normally, if I was a boy I would help him but as Susie I went in the cabin to help Janet with girl things. We fixed lunch and after lunch Jim and I went down to the dock to see the lake. Jim was doing something to the boat and I was standing on the dock when all of sudden Brad showed up. He was a boy my age from down the lake. Just a month ago he and I had been water skiing and hanging out on the lake. I was in shock. What was he going to say? Here I was dressed as a girl. To my amazement he looked right at me and then turned and said hi to Jim and asked if Billy was here. Jim smiled as he looked at me and told Brad Billy wasn't here. Then he introduced me as Janet's niece Susie. Brad smiled and said hi and I smiled back and greeted him. He started to ask where I lived but Jim seeing my distress interrupted him and said we had to get going. I almost ran off the dock but I still looked back as we left and saw Brad looking at me. He had a look like he was undressing me.
When we got back to the cabin Jim told Janet about our encounter with Brad. She teased me and asked if I wanted to invite him over for dinner. Jim told her Brad eyes almost bugged out of his head when Susie smiled at him. Janet said she is a real flirt this one. We should invite him over but not for dinner. Jim said you two girls could have "him" for dinner. Ooh that sounds good another cock would suit us fine right Susie. I just nodded then Janet said speaking of cocks I'm horny lets go in the bedroom. We all went into the bedroom. It had one large bed. Janet said come on Susie let's get undressed we've got some serious cock sucking to do. Jim's cock was already hard when he got on the bed. He lay back and Janet and I got on either side of him and started to suck him off together.
After we sucked his cock a few minutes I asked if I could be fucked like a girl. I saw Janet's eyes light up. I don't think Jim fucking me was planned but I knew how much it excited Janet the night before so I thought it would excite her even more if I suggested it myself. It did and she was all for it especially if he got me in the missionary position "like a girl". I lay back on the bed and Janet put a pillow under my ass to get my hole up where Jim could get his cock in me easier. She got some cream from her dresser and put it in my asshole. She sat beside me at my head. I put my legs in the air and as Jim started to put his cock in me. Janet warned me it was going to hurt again. God it burned when he penetrated me but it soon was all right. I could feel him filling me up with his cock. He has it all the way in now sweetie Janet said. Just relax and feel him fucking you. As Jim pounded away on me I grabbed Janet's tit and started to suck on it. She took my hand and put it on her pussy and I began to finger fuck her wet cunt. She was exhorting Jim to fuck me and bouncing up and down on my hand. Then she grabbed my already hard cock and started to jack me off. Jim let out a grunt and pushed as deep in me as he could and I felt him shoot his load in me. At the same time I shot my load all over my stomach. Janet ground down on my hand and got her orgasm about then too. Jim pulled out and Janet started to rub my cum into my stomach and chest. She told me I was a very good girl.
We spent about another hour fucking and sucking each other. I got to fuck Janet in the ass, which was a new and pleasurable experience for me. We got cleaned up then and got ready to leave. The next day was Sunday our last day together before I had to go back to school.
That evening Janet came in the spare bedroom as I was getting ready for bed. She sat down on the bed next to me and thanked me for playing her daughter for the last few weeks. She said tomorrow that I needed to go back to being a boy. I could keep my female things here in their spare bedroom and I could come over any time and play dress up. I could also play with her but I was a boy and I needed to concentrate on that. I said I understood what she meant and I told her I loved her. We hugged and I went to bed.
The next day I went back to school. I still visited her when I could. It seemed we were both busy a lot and our love making sessions got further and further apart. I met a girl in school and started dating her. I used some of my expertise that I learned from Janet on my new girl friend. She was impressed with my sexual prowess.
That Christmas Janet got me a special gift. She got me three pair of lacy bikini panties. I got to model them for her and while we were making love I told her about my new girl and that I was having sex with her also. She didn't say but I don't think she was happy about that.
That next summer Janet found out she had lung cancer. She was a heavy smoker. I was devastated. She died that fall. It nearly killed Jim. That was his second wife to die of cancer. After the funeral Jim called me over to his house. He thanked me for being Janet's special friend. He told me he was selling the house and moving to Florida to live with his brother. He said Janet's sister was coming tomorrow to go through Janet's things. He said I could have any of her clothes I wanted and I needed to take my stuff out of the spare room. I thanked him and went into her bedroom and selected a couple of pairs of her panties. I also took the entire black ensemble that she caught me wearing that day. I couldn't take all of my feminine clothing home. I just didn't have enough space to hide it all. That ended my episode with Janet and Jim. I am still a crossdresser and I still have that black dress. It doesn't fit anymore but I still have it.