True Story my First Time with an Older Woman with a Difference

by Stephen T (Bristol)

Having finally left school I was in my first year as an apprentice and I had an accident at work and was sick for a while luckily it was summer. I had some friends I used to see a lot as we grew up and one in particular Anne was a few years younger than me but she was always a bigger stature than all the other girls her age and was unusually mature for her age and we hit it off.

I used to go around some days while of work and do some chores for her lovely mum who was 45 yrs of age , her husband had left her a few years earlier I could not see why as she was so nice. We were alone some times in the house when her younger brother was out for a few hours and mum had gone to friends and we developed into a relationship but only kissing and cuddling.

One day I was doing some gardening and I had my shirt off and her mum brought me out some squash she said my you have grown into a fine young man and that is some muscly physique you have developed and squeezed my big arm I just laughed. She said watching you I am beginning to worry as I am looking at a man and my daughter is very young I said you have no worries there as I respect her age and she is a very good mature young lady.

She said I wondered if she had had any sexual relations as yet and I said well if so I do not know how as I am the only boy she has been near and even kissed, she said thankyou and smoothed my long wavy hair. We all used to play games some evenings and laugh a lot her mum said she loved being around us and the laughter it made her feel young.

One afternoon her mum and I were alone in the house as brother had gone to friends to play for the rest of the day and they were experimenting with makeup as Anne was getting into makeup more now and her mum turned and said we could make you into a young lady also and laughed. Anne said yes that would be fun can we do it and I declined and her mum said go on I thought you were a bundle of fun, Anne said please let us so I reluctantly did.

It was quite a process the eyeliner, blusher and then the red lipstick and tied my hair up in a pretty silky scarf in a turban just the same as her mum usually wore and when they finished they said my word you look very feminine and pretty. Anne said mum can we take it further I said what do you mean , they were all of big stature and Anne said I bet we could find him a dress of yours that would fit, I said what if your brother comes in she said he is not coming back until 9.00 this evening.

Again I reluctantly agreed so her mum brought in this very pretty flouncy pleated summer dress and said what about this and I went red in the face. She said we may as well go the whole way for the effect and also brought in a full set of underwear bra, matching big full cut knickers, suspender belt and stockings and a full silky slip. I thought crickey what have I let myself into, her mum said go into the bathroom and slip these on but I will put the stockings on you as I don't want them ruined, so I did as she said.

God the felling was stimulating slipping those big silky knickers up my body and when her mum got between my legs and slipped the stockings up my legs and attached the suspenders that was electric, while attaching the suspenders her hand accidentally brushed against my pantied cock and it pulsed and I could see her look at it from the corner of her eye.

Then she produced some spare tights rolled them up and padded the bra out and said raise your arms and eased the slip down over my arms which was also a heavenly feeling followed by the dress she then produced a pair of high heel shoes and put them on me. Right stand up then give us a twirl, I stood up I cannot explain the amazing feeling that had engulfed me she said go into my rook and look in the mirror wow I looked stunning and Anne said I cant believe you look so feminine and even more so than me and said I feel a bit jealous.

I was about to start to undress when they said not yet stay like that a while so I thought that would be wonderful as I was getting lost in this new found silky nylon world, then we all went down stairs and chatted. her mum brushed past me a few times and came into contact with my now raging erection and looked art me I went into the kitchen and she followed then did something unprecedented and kissed me full on the lips.

She said I think you loving this much more than we are aware of and I think we have just awoken a part of you you did not know existed she then put her hand up the dress and squeezed my raging erection which was leaking profusely. She smeared it all over the head of my cock then put her hand up to her mouth and licked it all off I was quite shocked and she said I had better sort out that lovely cock I think.

She called Anne and said would you go to your brothers friend house to ensure he comes back please I said I cannot go as I have to get all this off so she reluctantly agreed. As soon as she was out of the house she led me upstairs sat me on the bed dropped to her knees gave me a fabulous french kiss. Then put her head up the flouncy dress pulled my knickers aside and took my cock and started to wank it then put it in her mouth and sucked it.

That was heaven my first time but not as I thought it would be, She sucked, gobbled and made all sorts of noises as she enjoyed my cock and she then pushed me back on the bed and turned opposite ends pulled her panties aside a plunged her sopping wet fanny right on my face and told me to lick it. The aroma and taste was something of the planet again a first and she led me through every part of this fantastic experience.

We both came in gushes like I have never seen and we licked and sucked each other clean. She then kissed me long and full exchanging smells and juices then she said we had better sort ourselves as they will be back in half an hour. So she slowly undressed me and when she slipped the stockings down my cock sprang into life again and she said god I have to have that in me turned around and put it in the entrance to her juicy fanny and plunged down on it she bounced up and own until she screamed and fell backwards on me as she came again.

She then got of me and we had to hurry and clean up and all the smeared make up of our faces. We then went back downstairs as the other two came back, Anne said you both look a bit flushed and we said we had to hurry to get all the make up of before your brother came home. That was the start of a long love affair and when we could be alone together over the next few weeks.

She taught me all there is to know and when she had her periods she would dress me wank me in her big grannie knickers up then suck me off and then share it with me. Sometimes she would dress me in her stockings and suspenders and full black sheer nightie and hair tied up in her black chiffon scarf, she loved to see my cock tenting her nighties and sometimes she would use her dildo on me if I let he.

What she loved best for us both to be fully dressed in silky nighties and stockings hair tied up in silky scarves and fuck all afternoon. Unfortunately I had fully recovered and had to go back to work and so it only happened now and then but I will always look back and remember our silky time which has never been repeated with anybody else. I only dream of it.