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Teacher's Pet

I taught in an experimental program and was partnered with an older teacher. She was about 60 and I was 45. I'd been crossdressing my entire life and passing since I was 16 but at school it was strictly underdressing: bra/cami and panties; jet black pantyhose/kneehighs; women's shirts and sometimes trousers.
One day I needed to borrow a car to bring some things to school and she asked if I could pick her up on the way. When I reached her apartment the door was left opened for me and she was in the bathroom. When she came out and saw me there she was wearing a white bra and blue halfslip and I kiddingly said something about how one's underthings were supposed to match, to which she retorted, "I'll bet yours do, don't they?". I didn't really know how to answer so I said "You'll never know".
Driving to school she mentioned how she knew I was a crossdresser simply by how I moved and how I always wore black pantyhose. Here I truly believed I was doing everything right, even making sure the light pink lipstick I put on every morning was off by the time I reached school. I was shook to say the least.
True, many people had seen me dressed as a woman and many knew me only as a woman, and those who knew I was a crossdresser, overwhelmingly said they preferred the woman to the man. So I was secure in who I was, but I was obsessive about keeping that part of my life away from my professional side and I thought I had done a good job, but my friend and colleague, Corinne, had seen right through my facade. She assured me however, that she was the only one on the faculty that knew and she admitted it was a kind of sixth sense she had. She could even discern who was gay and who wasn't and I was "discerned" as gay. I admitted it and she said "We'll see what we can do about that".
It was Friday and when I drove her home she suggested we see each other the next day and we agreed on one in the afternoon.
When I rang her bell I was wearing a plaid skirt and a black turtleneck with black hose and low-heeled pumps, and my Coach bag. All covered by a Burberry trench and a Chanel scarf. My hair, which is my own, was done by my salon on the corner as were my nails, and my makeup, which I did, was pretty darned good.
When Corinne opened the door you could have bowled her over with a feather. She looked as if she was going into shock, because she was not expecting Joanne to be standing there; she expected Joe with a little bag. She quickly recovered and we had a great laugh after a cup of calming tea for her. We sat and talked a while and she inspected me for any flaws and found none. I got the "coulda' fooled me" stamp of approval, and we decided to go down to the Angelika for an indie film we'd both been wanting to see. (Oh, all this happened in NYC.)
The film was wonderful and we decided on an early dinner at an Indian restaurant she knew . The owner greeted us with opened arms and  I was introduced as her "neice". Her niece? Why not her colleague; her friend; her neighbor? it just surprised me and all she could say was that it was the first thing that came into her head. I went along with it; I had to, there; but at the table I told her I was not going to call her "Aunt Corinne". That behind us we decided to go out for a walk and it started to rain. We were in the Village by then and hustled to my apartment to dry off. Once there she began looing all around abd was amazed at how it looked exactly like a woman's home with barely a trace of masculinity in it. And she was more amazed at my wardrobe, and the paucity of male garb. She was especially interested in the sizes which were close to hers. She said "if we become girlfriends we can borrow each others things". I thought that was cute.
She tried on a few of my things and I must say she did look good in them and I enjoyed seeing her in them, and getting into them.
And then she dropped the bombshell: "Are you really gay or maybe just a bit bi?" The reason she asked was that she was feeling an itch and really wanted it scratched and I was the perfect candidate for the job. She came over and kissed me and put her hand on my right breast which was all mine as was the left one and she was amazed that I actually had "real boobs". She led me to the bedroom and began undressing and strongly urged I do the same. For a woman her age I had to say she had a beautiful body and as soon as I was out of everything she was on her knees and going to town on me. After a while she looked up and asked if any guy I was ever with was as good as her? She was good! I've been told by many of my partners that I give fantastic head and I know guys who do likewise but I must admit Corinne was near the top. She stopped short of my ******* and laid on her back, spread her legs and said "Your turn". It had been a while since I ate a ***** and I was afraid I  wouldn't be up to her standards but once I got into it I had her moaning and screaming and calling me all sorts of cocksuckers. I brought her off and I was afraid the neighbors would start knocking on the wall, so I didn't prolong it.
We rested a bit and then we ******, followed by another rest. Hey, we weren't kids. Then she found some KY and spread some over her ******* and guided me in. It was like she was just reamed by a  horse, it was so easy going in and she loved it. She ightened up  and got another fantastic ****** out of me. After another breather she went exploring and came back with a strap-on that I save for friends who can't take Viagra. In  no time she was ******* my brains out, and she admitted that she was bi as well and had a few strap-ons at home.
After we'd exhausted ourselves and showered she decided to spend the night in order to have a good excuse to borrow some of my clothes becuse she couldn't be seen in the same outfit two days in a row.
Sunday morning we were both still sexually satiated and so we got dressed and headed out to brunch followed by a subway ride uptown to her place. When we got there her son was there and wondering where she was. She introduced me to him, and this time as a teaching colleague, and I have to say, he was cute and I detected a glimmer in his eye  towards me. Oh, boy, could I see complications in this one.
But all went well and after a while I decided there was a lot of school work needing to get done before Monday morning and I bid my fond adieus to Corinne and Michael. More about him some other time.
The  next day we went about our duties as we normally did and she wore the blouse she'd borrowed the day before. It didn't count if I was the only one who knew she'd worn it Sunday.
Our affair blossomed, even after I left secondary teaching to pursue a job at the tertialry level, and Corinne retired. We contined having wild sex and truly becoming "girlfriends with benefits", even traveling together and sometimes being seen as a pair of aging lesbians. That one I liked but she wasn't too wild about it. Dear Corinne died at age 78 and we continued our sex up to the very end, and Michael and I still see each other once in a while
josilver josilver 56-60 3 Responses Oct 10, 2012

Your Response


After becoming a widower I have begun returning to crossdressing and would like to find a friend like you

Great story. I like hearing that, even as a gay male, you could satisfy her sexually.

You seem to have found a soulmate I that Lady-my music teacher was like her( neither of us were openly Gay, but we couldn't do without men's company sexually)