Aunty Helped me to Crossdress

by Stephen (England)

It all started when I was 50 and my aunt who is 70 yrs very smart and very fit came to stay a few months after her husband died. My wife was working we watched the telly and I always thought her a bit prudish and the programs she now likes to watch when she can are sex related.

It seemed she knew very little about it and she never had full sex with her husband. I let her watch in my house when she was there and she used to ask me all sorts of questions it appeared she knew nothing about it.

I used to answer her questions and they became more risqué as time went on. Anyway one evening when my wife was at work she offered to take up a new pair of jeans for me. She said you will have to stand on a chair so she can take them up.

So I did then still standing on the chair she said slip them off so I did I could see her looking at my crotch and she said I am thinking things I should not. She said I have never seen another man’s cock up close and wondered what yours was like as my husband’s was only 2 inches long erect so we never really had sex.

So I pulled my pants to one side and let it fall out she gasped and ran out of the room in panic not expecting that. I said you were asking me really to show you so here it is she came back in and slowly put her hand around it and it grew instantly.

She was mesmerized and started to caress it, wow she said is a whopper so magnificent. Slowly she wanked it and got very carried away and said she loved it especially when it spurted all over her hands. She liked to do it every at every opportunity.

She said she had never seen a dirty book or film as soon as anything to do with sex or swearing her husband turned it off. I asked her if she would like to see an excerpt from a porn film and she said yes, I said it will probably shock you but she said to do it so I did.

She was shocked but was visibly stirred by it and became very restless especially when one part a guy appeared fully dressed in lingerie and stockings then she went of the scale clearly turned on by it.

I said you are getting hot under the collar loving watching that. She said that was the most sexy thing she had ever seen and said would you do that for me, I said what do you mean she said dress like that. I agreed but only at her house.

I said I do have some lingerie as I do like it anyway she was very surprised. When we were alone at her house for a few hours I let her dress me up. She had a nice wig from a fancy dress party she went to and made me up with full make up then tied my hair up in a beautiful silky headscarf in a turban.

She made me parade around and loved to hold my cock in the big panties and wank it oozing with precum then she surprised me took it out and put it in her mouth like on the film.

I have never seen a woman get so carried away sucking a cock before and she was making all sort of noises blowing and sucking it and she sucked till I came in her mouth and she slavered the lot until I was totally clean then she kissed me.

She said you have opened my eyes to something I should have had 45 years ago and cried as she had missed so much. I loved her and we became great lovers always both dressed in lingerie and stockings but there was one problem she was so anatomically small she could not get my cock in her no matter how we tried.

So she was satisfied just rubbing up and down her fanny and 69ing. She loved to wrap a silky scarf around my cock and wank me then finish me off by mouth.

She saw a couple more of my films and saw one where all the women loved it in the anus before I knew it she was astride me and lubed and sat on my cock right to the hilt, god she was amazing and that went on until she was 87 yrs old.

She had the most amazing pert breasts with no sag at all just like an eighteen yrs old and loved to wear see through nighties to show them off to me and she bought me see through nighties to wear and loved to see my cock tenting them. God I missed our time when she had to stop but will never forget them.