Transformation

Over 30 years ago after my divorce I developed a deepening friendship with an older woman I met at bingo. Doris was 62 at the time ,a vivacious slim widow with shoulder length silver hair and an easy laugh .I was 32 then ,a quiet somewhat introverted guy but when I was with Doris I felt totally alive and at ease.



We met often for coffees, then dinners out and at her home ,at bingo of course and I found myself spending more and more time with her .I noticed after a year or so our glances met more and more often and she tenderly often touched my arm or made sure she made an affectionate gesture. One evening while sipping wine together at her place one thing led to another and we ended up in her bed kissing. Things increasingly became passionate and we ended up making love .We admitted we were now romantically involved and things heated up from there .We became a couple and sometimes people gave us odd looks in public due to the age gap if we held hands or walked together as a couple. The sex was deeply satisfying and she had a high sex drive for an older women so we made love 3-4x a week .As we were deeply in love I moved in with her and found the sex and companionship the best I had ever known. We got married in a small civil ceremony and as we were both private types we did not socialize much except with another older married couple she knew who accepted us .Now we were husband and wife at this point and she was 65 while I was 35.The age gap had no effect on me as she was just the woman I loved and she felt the same about me .We had 15 loving years of marriage together before her kidneys began failing and she had to go to a nursing home. This was very sad and painful for her and me as we were apart as she needed much care .I visited her every chance I could but she passed away within a year of being there .I felt a deep loss and had no desire to date other women for a long time.

I lived in the same house and kept her clothes and items around as memories. Around 5 years ago I was a bit drunk one night and went in the closet seeing one of her sheer whit nightgowns .It reminded me of her and I felt an urge to put it on .I felt this wave of arousal with it on and my cock became erect. I looked in the mirror and felt this strange feeling that I could become Doris in a sense and this would keep her memory alive but be arousing as well. I ended up masturbating into the bathroom sink as I lifted up the nightgown. After this I began wearing her nightgowns to bed every night and around the house. When I smoked a cigarette I began emulating the way she held a cigarette and smoked it. I did this only at home .Deep down the feelings of becoming Doris intensified. I let my hair grow long and it was silver in color like hers was .I grew it to the length she liked it .I began waxing and shaving my body so I was smooth all over .I did not need to wear make up or bras, or other female attire as I identified as being a man primarily and this was more an emotional and sexual release. Wearing the nightgowns ,having longer hair and being smooth was enough as well as softening in my demeanor .This transformation began affecting my sexual preferences .I began noticing other men especially men my age or older and finding myself attracted to them sexually .I would masturbate picturing myself as Doris necking with one of these men and having sex with them. I began watching mature porn where older men and women had sex and imagined myself as the woman. Gay porn did not work for me at all as I needed the female image. These fantasies went on for several years increasing in intensity .Finally I had to live it out in real life.

I went on a gay site and noticed one day there was an ad from an older divorced guy seeking a man his age who liked the feminine role sexually .I contacted him and arranged to meet after a lengthy phone chat .Bill was 65 while I was 62 the same age Doris was when I met her which felt perfect to me .Bill was fine calling me Doris and he knew the context of my desires for role play and it seemed to excite him .We met at a cafe and I was dressed normally .We both liked what we saw in the other and I sensed attraction .Bill is taller than me a bit heavy set with short brown hair streaked with grey and a well trimmed moustache .I have become slimmer over the years and watch my weight carefully.


We got back to my home and I transformed into Doris as he sipped a rum and coke .I entered the living room and his eyes lit up .I had one of Doris's black lacy teddies I felt myself softening and we ended up slow dancing to some jazz. Bill kissed me softly and we necked up a storm. Later in bed I caressed him all over as he did to me and I went down his body and took his hard 6 inch cock into my mouth. He was circumsized and clean and I loved sucking him .I found myself kissing and sucking his cock urgently until he let go and blew his sexy load in my mouth .I finished Bill off and lay back to have a cigarette .He told me he really enjoyed it and even wanted to sleep with me that night to cuddle and kiss some more Throughout our time together he called me Doris and I softly called him Bill darling. He offered to masturbate my "clitty" and I let him milk my smaller cock to orgasm before we went to sleep. This was over 2 years ago and we became steady lovers in the meantime which is timely due to the pandemic. Bill and I progressed to making love and I enjoy how his cock feels inside of me when he makes love to me in the spooning position side by side or from behind .He always cums inside of me easily as he says I am tight, wet and sexy to fuck .I think the fact both of us identify like a male female couple sexually intensifies the pleasure for both of us. When we go for drives we find somewhere to neck and I blow him in the car .At night I am sure if people saw us in the car necking my longer hair would make it look like I am his woman visually from a distance. More and more I feel like I am loving Bill like Doris would love a man and I like the feeling a lot.