Author: Lovercraftbeyond

[MF] Diana(55) and her first anal experience.

If you have read my previous stories regarding Diana you will know we were work colleagues who were friends and then had entered into a friends with benefits relationship. I was 23 years old 6’3, tall and handsome she would say. Diane was 55, about 5’3 chubby with short blonde/greying hair and most importantly huge G-cup breasts, saggy but still full. She was divorced, had two children and was very sexually inexperienced. Her husband had been older than her and a missionary only kind of guy.

After 3 months of being hooking up Diane had tried multiple sex positions, had experienced oral sex, (giving and receiving) for the first time and regularly tit fuck her. (You can read the previous encounters on my profile.)

She was really coming out of her shell. At first when she wanted sex she would say “Do you want to go upstairs” then she started saying to me “I want you to do me” and after about 7 months she would text me. “I’m waiting for you lover, come and fuck me”. She had bought some lingerie (which was slightly too small and her breasts would spill out of). She had a vibrator now and she was getting better at dirty talk. She would call me her toy boy. Read more »

[MF] my first experience with an older woman. M23 and F55

(I recently deleted my old account and I am reuploading my stories)

Hi, this quite a long story but I wanted to share this story from my life. I hope it will give you all an appreciation for older women and how amazing they can be.

When I was 23 I was doing shift work at customer service centre, day shifts and night shifts.

I worked with team of 5, me and 4 other women. All nice people but I wasn’t planning to date any of them. One was Diana (not her real name). She was 55, about 5’3 with short fading blonde hair, blue eyes and slightly chubby but nice skin and she wore nice makeup. You could also tell she had an impressive set of breasts under her clothes, but you try not to look. She had been working there for years and I had only been there 6 months.

We didn’t speak much as we were mostly on the phone. She lived near to the building and walked to work but I had drive in. I was still living with my parents at the time, saving for my own place. One day after a night shift and it was awful weather outside, wind and rain I offered her a lift home which she accepted. I dropped her off, she thanked me and I continued home and didn’t think anything of it. Read more »

[MF] Holiday Hookup with a Married Woman.

[MF] Holiday Hookup with a Married Woman.

Holiday Hookup with a Married Woman.

This is not a true story just a fun fantasy I played out with a sexy cougar on reddit. They know who they are 😉. I thought I should write it out and expand on it.

I was holidaying in New Jersey, USA. I was travelling alone, I felt I needed a break from all the drama back in the UK. I had a nice hotel, plenty of spending money and I intended to have fun, relax and clear my head.

About 13:00 I was just in the town browsing some stores and while look at clothes I stepped out in the isle without paying attention. I walked straight into someone and knocked them to the ground. I am 6’3 and this person bounced off me and on to the floor.

“I’m so sorry” I said immediately, apologies come automatic from the British. I looked down and saw a woman in a blue dress sprawled on the floor, her shopping falling out of its bag. I got on my knees and immediately helped her up and put her shopping the bag. Read more »

[MF] My continued relationship with an older woman. Reupload

Due to multiple requests, I have decided to write more details about the experiences myself and Diana shared. As you know Diana although was 55 years old and two children was very sexually inexperienced. To her sex was just missionary and the occasional blowjob, she had never received oral or tried new positions. Her husband had left her for a younger woman. Diana she was lonely, depressed and hugely lacking in self-confidence.

About one month into our sexual relationship, we started to try new things, up until this point it just been missionary sex usually followed by me going down on her. Diana still wasn’t very good at what I would consider dirty/sexy talk. Her way of asking for sex would be ‘Do you want to go upstairs?’. I would drop her off after work, she would invite me in for a cup of tea and we would kiss and cuddle and sometimes she would ask if I wanted to go upstairs. I never said no.

Diana wasn’t comfortable with the lights on during sex so after one session and we were both snuggled in bed. I asked her “Wouldn’t you like to try it with the lights on” Read more »

[MF] my first experience with an older woman. M23 and F55

Hi, this quite a long story but I wanted to share this story from my life. I hope it will give you all an appreciation for older women and how amazing they can be.

When I was 23 I was doing shift work at customer service centre, day shifts and night shifts.

I worked with team of 5, me and 4 other women. All nice people but I wasn’t planning to date any of them. One was Diana (not her real name). She was 55, about 5’3 with short fading blonde hair, blue eyes and slightly chubby but nice skin and she wore nice makeup. You could also tell she had an impressive set of breasts under her clothes, but you try not to look. She had been working there for years and I had only been there 6 months.

We didn’t speak much as we were mostly on the phone. She lived near to the building and walked to work but I had drive in. I was still living with my parents at the time, saving for my own place. One day after a night shift and it was awful weather outside, wind and rain I offered her a lift home which she accepted. I dropped her off, she thanked me and I continued home and didn’t think anything of it. Read more »