(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.
The next day it was bad weather again and as I was driving in I saw her walking in the rain, I pulled over and offered her a lift which she accepted again. This continued quite a few times, if I saw her I would offer to pick her up or if I was going home I would drop her off on my way. We kind of got stuck in the routine of it and I couldn’t really stop as it would feel rude. However it was nice to chat with someone outside of work even if it was only for a few minutes.
This continued for a few months and we got to know each other a little better, she was divorced, two grown children, a son and daughter. The son was at university and the daughter was living in an apartment with her friends. We would talk about work and how much we hate customers/managers etc. She would ask me about my relationships, I said I wasn’t in one at the time and I would ask her about hers, she said she hasn’t dated since her husband left 7 years ago. He had left for a younger woman.
The more we talked on these journeys the more she would open up, she was lonely and although she had friends she lived alone, didn’t have any pets and her children didn’t visit that often. I think she was going through a bit of a depression. I kept trying to cheer her up but it wasn’t really working, but on the week before valentines day after dropping her off after the day shift she burst into tears in the car, her husband was taking his new wife on a cruise for valentines, her friends all had partners and she felt real low, she felt unattractive and desperately lonely.
I felt very sorry for her and since we were going to work the night shift on valentines day I said why don’t we meet earlier and go for dinner before work, my treat. She said I didn’t have to but I said I wasn’t doing anything on valentines either. She agreed and we had a very nice meal on valentines at local bar/restaurant. We weren’t dressed up particularly just in our work clothes but the food was nice and we had laugh moaning about work and relationships. She asked me about my relationships, I said I had been with a few woman and even a guy at university. (If you have read any of my previous stories you know I am bi) but no one serious. She was surprised but seemed okay with it, she said she her husband was her only partner, she got married when she was 20.
After the meal I took her to work and we did our shift and then I took her home, she thanked me for the meal and kissed my cheek and I went home. That became a new thing every time I took her home she would kiss my cheek. I was feeling quite close to her and after two weeks of this I turned my head when she kissed my cheek so she kissed me on the lips. She pulled away immediately, got very flushed and apologised. I told her don’t worry, entirely my fault and winked at her. She smiled and got out of the car.
Nothing else happened for about month when again she was in very low mood, I dropped her off after the day shift and she was obviously upset. It was something to do with her ex-husband and her children meeting up without her. She was feeling lonely, I offered to go inside with her and make her a cup of tea.
We sat on her sofa and I made her the drink we talked and I held her hand, she talked about being lonely and how she had been trying online dating with no success. She felt unattractive and wouldn’t find anyone. I told her she was being silly, and hugged her. As I hugged her I kissed her softly and felt her start to kiss back but she pulled away. She said I didn’t need to do that, she was older than my own mother and there were grandmothers her age. I said yes but they aren’t as hot as you which made her smile and I kissed her again. It was just kissing on the lips but no tongue or anything but it was nice. We broke the kiss and said she had things to do and I should go home. She thanked me for the lift and I went home.
Everything continued as we usually did for the next few days, with me picking her up until the last day of the day shifts. She asked if I wanted to come in for a cup of tea, I was happy to. We had tea and we sat on her sofa and she thanked me for the kiss but this was silly and I didn’t have to pretend to like her. I said what if I did like you? She said I am too young, we couldn’t be in a relationship. I told her we didn’t have to be, maybe we could just have some fun together. I held her hand and kissed it. She said she didn’t know what I meant, I moved closer and kissed her lips and asked her don’t you miss sex? She looked very embarrassed at that and didn’t say anything. I felt I needed to be blunt so I kissed her again. I asked her, do you want to have sex with me? She didn’t look at me but she nodded and continued to hold my hand. I said do you want to go upstairs? She nodded.
I held her by the hand and led her upstairs, she opened her bedroom door and we went in. I kissed her and she kissed me back, the first time our tongues touched. All the lights were off so I couldn’t see much. I started to undress her, I took off her clothes until she was just in her bra and panties. I undressed until I was naked, my cock was hard and I stood close to her. She said she didn’t know what to do, I said she could touch me if she wanted. She put her hands on my chest and felt down me and my stomach until she touched my cock. She pulled her hand away quickly and I said it was okay and put her hand back. She just held her hand on it, I kissed her again and undid her bra. I could just make out her massive breasts, they were a large G-cup. Saggy but still very full with large erect nipples. I have never been with a woman with bigger breasts they were huge. I told her she was beautiful and hugged her. I asked her is she wanted this, she said yes please. I guided her to the bed and she lay down and I climbed on top of her. I kissed her lips, her neck, her shoulders while she moaned quietly. She ran her hands over my shoulders. I moved down to her breasts, I kissed and licked them. I took one of her nipples in my mouth and sucked it gently while squeezing her other breast in my hand. She moaned and said that feels nice. I did this for a while, swapping from nipple to nipple until I moved down to her panties and pulled them off. She was hairy down there but I didn’t mind. I moved my face to her pussy. She asked me what I was doing, I told her to relax. I began to lick and suck on her pussy and clit. She moaned loader and put her hands on my face. She kept saying, what are you doing? Oh my god what are you doing. I kept doing this until I felt her legs start to quiver and shake. I sped up until she cried and out and arched her back when orgasmed.
I moved up her body and lined up my cock and slowly slid insider her, she was soaking wet, warm tighter than I expected and felt really good. She groaned and I buried my face in her chest, kissing and sucking on her huge tits. I fucked her slowly and gently, we hugged and kissed and I told her how good she felt, how hot she was. She just moaned and writhed beneath me, she didn’t really know what to say but I didn’t mind. Because it was so slow it took me a while to cum but eventually I felt it building so I sped up and asked her if I was okay to cum inside her, she said yes. She hugged me tight as I did. I rolled off her and we cuddled naked in her bed. It was really nice. She thanked me and said she had never felt like that. I told her I would love to do this again if she wanted. She seemed surprised but said yes she would love too. Over the next few weeks we would have sex whenever I took her home after the day shift. It transpired she was very sexually inexperienced. Her husband had never gone down on her, she had only sucked his cock twice at his request and he was missionary only. I told her we could do whatever she wanted, at first we just repeat what we had done the first time but eventually I wanted her to leave the lights on because I wanted to see her body. It took a while before she built up the confidence but once she did she loved it. It turns out her breasts were 44Gs.
She was happier and started to talk dirty during sex, she gave me a blowjob on her sofa. She had never heard of titfucking but she let me do that to her which was amazing. Over the course of a year we fucked so many times, she tried riding me, she doggystyle which became her new favourite. We fucked all over her house, the kitchen, the lounge, the shower, on her dining table. She wanted to try anal and we did, it took a while but she started to really love that and it became a regular thing for us. Sometimes she would ask me to come over early before work to have a quickie.
She really came out of her shell, she was more confident, she bought herself lingerie and even a dildo which I would use on her. I loved making her happy, making her orgasm. She enjoyed having a secret toy boy and although we knew it couldn’t last we had great fun together. It gave me my appreciation for older women. This went on for almost 2 years before I changed job and we had to stop seeing each other. She is with a guy her own age now I think so I am glad she is happy.
Thanks for reading.
Happy to share more details or if you have questions please feel free to AMA
Source: reddit.com/r/gonewildstories/comments/10csvkl/mf_my_first_experience_with_an_older_woman_m23
Great story