The Lady Down The Street

That lady whose house I would cut the grass who left her shoes outside. One afternoon I had gotten my hands on a Bikini a few yards down from hers and was wearing it when I went into her yard; she had high bushes which concealed the yard. I was working my way around the edge to see if her car was in the driveway. If she was gone I could layout wearing the bikini. Since she had a lounge chair in the backyard she would stretch out on. Before I go on let me tell you about her, retired teacher, she was 5'7, about 120lbs, below an A cup in breasts and wore size small panties, but a size 9 shoe, and she wore some very sexy clothes for the time period middle 60's. Back to where I was got up the side and looked around and there was the car. I froze and started to back away. When just then she walks out her back door wearing her own bikini which I had tried on in the past too. Goes to the lounge chair and sits down, lays back and begins to read a book. I couldn't go forward cause that meant the front yard, and trying to get out the back way meant walking right past her. I decided to try the front yard. I walked up to the end of the driveway and looked around no one in sight as I walked out the mail truck came around the corner so I ran back into her yard and hid by the wall. The bikini I was wearing had bright flowers all over it. I moved back to the backyard she was now laying there with the book on her chest wearing sun glasses. I couldn't tell if her eyes were open. I decided to take a risk. I took off the bra piece. And placed it in the bushes. Then walked along the edge hoping that she was asleep. I got part way when I heard Hi. I turned and smiled and said I was checking to see if I needed to cut your grass. And apologized for awaking her. She waved me over, and walked over to her. Remember I said she had no breasts per say just nipples. I could see them perfectly from where I stood now. This caused me to pitch a tent. Since I was wearing a nylon bikini panty it was very visible. She just said maybe next week you can cut the grass. With her dark glasses I couldn't tell where her eyes were looking. As I scanned down I could see her hair sticking out from the bikini panty. She said it is so hot out here today, I agreed. It was about 11am, and the sun was really starting to get hot. She then said come and have some lemonade with me. She swinged her legs over and got up, and insisted I have some with her. We went in the backdoor which lead to the patio then from there you walked in the kitchen. She serves us 2 glasses of lemonade then tells me she will be right back. She goes into the bedroom side of the house. When she comes out she sits down and starts to ask me all kind of questions. This is the summer of 1969. After about 30 minutes she gets up and takes away the empty glasses. Then reaches for my hand and said come with me. We walk back to her bedroom there on the bed was a complete set of matching bra, panties and garter belt, with silk stockings. She places her arm around my shoulder and uses her free hand placing it under my chin and raises my face up. She looks into my eyes and said I know you have been wearing my clothes, and taking my shoes at times. I don't know whose bikini bottom you are wearing right now, where is the top? I told her in the bushes outside. Then she told me she had seen me when I entered the yard. And that she went outside to catch me in the act. I just stood there frozen. She pulled me over to the end of the bed and sat me down. Now tell me the truth. How long have you been wearing women's clothes? I told her since I was 8. Whose clothes had I been wearing? I told her my mother's, aunts, and those up down her alley off the clothes line. How long have you been wearing mine? I said about 3 years. She said OK now do you like boys? I said kind of. I told her what had happen to me with the drunken guy who screwed me. She then asked if I liked girls too, which I said yes I do. She told me to stand up; she had me spin for her a few times. Then she said you have very sexy legs, nice buns, you have a waist like a girl. Your hands look female. She studied my face some. Then without a word she pulled down the bikini bottom. Exposing my ****. I had hair not a lot of it. She just made a frown and said I can shave you. She had me turn around facing away and she placed her hands on my bottom feeling my cheeks, then her fingers went between my cheeks. She just said perfect. Told me to kick-off the bikini and to come with her. I followed her to bathroom, she had me sit on the toilet, open the cabinet under the sink and pulled out an electric shaver, she said extend your legs. She then lowered herself and started to shave my legs and feet. Once complete she said stand up, she lifted my **** and shaved me completely, then had me turn around and she shaved my cheeks and had me bend over and she shaved between my *** and legs. She grabbed a bottle off the counter and started to place cream on me. Once done my skin was smooth as silk. It felt so wonderful. She took me back to the room and told me put on the set on the bed. It was purple and black set with plenty of lace on the edges. She then went to her closet and pulled out a dress that I had only looked at because I was afraid of staining it. It was knee length with spaghetti straps. The color was a dark blue with highlights of black in the thread. I felt so sexy wearing it. Then she brought out a pair of 4 inch spike in black, now she had wood floors, and she didn’t wear shoes inside the house. She said its ok go on put then on. Once on I loved the clicking of the heels on the floor. She had me sit at her vanity and she did my makeup. Then she went beck to her closet and pulls from the top shelf a shoulder length wig in a rick brown color. When I looked in the mirror on her door I was thrilled, overjoyed and anything you can up with. I was a woman. She led me to the living room and had me walk back and forth a few times the heels just drove me crazy with the clicking sound. She told to sit on the sofa; she went back to her room. When she came out she was wearing a long robe tied at the waist. She sat down next to me and said you look so very beautiful. Then she leaned in and kissed me on the lips, softly then she open her mouth and slipped her tongue into my mouth. As I was kissing her she undid the tie and opens her robe she was completely naked. She took my left hand and placed it on her right ***, the nipple was like a pencil so very narrow sharp but hard, she broke the kiss and told me to suck on it. I did as she requested. I was able to get the whole thing in my mouth and suck on it using my tongue to twirl the nipple. She said do both of them. So I did moving back and forth between them. She opens her legs and placed my hand on her hair and said feel me. She was soaked her hair was moist completely; I worked my way into her hair and her lips, as I touched them she let out a deep breath. She pulled me back to her face and kissed me again but with more fire. She then told me to get on knees in front of her. I do so and she open wide her legs and said lick me now. I moved in towards her ***** the smell was so strong but sweet. As my face got closer she placed her hands behind my head pulled me into her awaiting *****, I started to lick and she started to grind her ***** into my face. My neck felt like it was about to break. She began to say things like lick me you little ****, you’re my ***** now. Eat that ***** you sissy *****. Then she lifted high off the sofa and told me to like her ******* I just couldn’t get to it, she pulled away abruptly and flipped over resting her knees on the sofa and reach behind and spread her cheeks open now lick my *** *****. I moved in and stuck out my tongue and started to lick her cheeks she said no my ******* ****. I worked way in and found it, the taste was so musky and sweet at the same time she let out a sound as I hit it the first time. Then it Oh yes eat my *** my sissy *****. Stick your tongue in me I was actually enjoying it, then she said lick my ***** when I did I found her hand had been finger her *****. She hit the organism just as I went back to licking her *****. It was like I ******* her *** with my nose. The taste I was getting was pure heaven. After what seemed a very long time she told me to sit next to her. She turned and wasted no time in kissing me and sucking my tongue into her hungry mouth. For the first time she reached down and touched me and felt the hard-on I had. She got up and told me to come with her. We went back to her bedroom; she pointed to the bed and told me to get on stomach. I do so she walked over to her nightstand and open the drawer and pulled out a *****, I had never seen one before. She got up at the end of the bed lifted the dress up exposing my panty covered ***. She pulled the panty down partway then buried her face in my *** kissing and licking me, she spread my cheeks apart then proceed to lick my *******, it felt so good, when she got her tongue in I loved it and raised up for her, she then started to finger me, before I knew it she had 3 fingers in me, your just like all women she said. Then she pulled them out and she placed the ***** in my ******* opening and pushed in, it hurt but she wasn’t stopping and she got it in. Then she pumped it deep and long it felt like when that guy have ****** me, but it also felt good. She buried deep in me then told me to roll over, she lifted the dress up and exposing my ****, she straddled me and sat down guiding me into her *****. Having the ***** in my *** and her on top made me feel so dam good. She started to bounce and down and the ***** was pushing in every time she came down. All of sudden I couldn’t hold it and I shot my *** inside her. She yelled out you’re my *****. Once I had finish shooting inside of her she popped up and climbed up and placed her ***** above my face. Then she flexed her ***** and *** oozed out landing on my mouth, swallow it sissy ***** she said. Then she lowered her body until her ***** was now covering my face completely, lick me ****. I could taste her *** my *** it was wonderful She hit it again the organism made her go nuts ******* my face. When it finally subsided she climbed off me. She told me I could come over and dress for her and that she would teach me how to apply makeup and that she would make me the perfect girl. So for the next 2 and half years I got to enjoy her company and her clothes.
deleted deleted
26-30
11 Responses May 23, 2012

That was quite an awesome experience that surely cemented your life enjoyment of cross dressing. Have you ever gone back and shared experiences with her later on?

I wish I had that

so sweet lovely teacher i wish to be with you ,,ill be in heaven...i love mature my dear Francesca you are great..kissssssssss

Good story, very sweet. I wish it were me. You're very lucky. :) <3

One lucky gurlyou were fi this story is true. Some folks just have all the luck.

OMG....hot as hell!!!!

Baby-Baby-Baby- You had to be in Heaven. I know that I would have been. What a time that must have been.

what a great story I wish I had a older woman to help me dress when I was a teen.

sounds like you had a great time of your life. IS she still around to play dress up with.

i am literally shaking at how amazing all of that would feel. i can barely type what i want to type

so wish i was you