Thank you all for your upvotes on my story about myself and Diana. I really appreciate the feedback and I am glad you found the story as wholesome and sweet as it was for me in reality. I hope more guys can appreciate how sexy and wonderful an older woman can be.
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”
“Not really” she replied
“May I ask why not?” I asked.
“I hate my body” she said looking away from me “I don’t want you to see it in the light”
“Why?” I asked “I love your body, can’t you tell?” I let my cock press into her skin. At 23 years old my cock was always ready to go straight away.
“It’s old, fat and saggy. I don’t want you to see it like that” she said sadly. Diana was 55 and she was a little chubby but I wouldn’t call her fat. Her breasts were 44G cup and they were saggy but they were still plump and round. Veiny with large nipples. I loved them. She had wrinkles but her skin was still pale and clear, she didn’t smoke or drink anymore. She looked good for her age with a very womanly figure.
“Not it’s not” I told her, I rolled closer to her and put my hands on her breasts and started to massage them. “You have fantastic tits” I said “I love them”
“I hate them, they are saggy and they hurt my back” Diana said. I put my lips to her nipple and started kissing them. I rolled on top of her and gave each nipple an exaggerated suck. I gently slid my cock inside her making her gasp slightly. We kissed and made love again, gentle sex. I paid extra attention to her breasts and made sure to pinch her nipples and lick them and squeeze them together. After I came inside her again and it was time for me to go, I got dressed and she put on her robe and walked me downstairs. She always kissed me at the door before I left.
“Same again tomorrow” I said smiling, I picked her up and dropped her off for every shift we had together.
“Only if you want to” she said.
“I can’t resists those breasts of yours Diana, I’ll always want to” I gave them a squeeze through her robe playfully “I’d kill to give you a titfuck”
“A what?” Diana asked.
“You know titty fucking, fucking your breasts” It was obvious she had now idea so I laughed and said “Google it”. I kissed her again and left.
Later than day I sent Diana a text saying I was looking forward to seeing her again tomorrow and I missed her. She replied I miss you too and then text me to say “I’ve read all about it now on Wikipedia, it’s called Mammary Intercourse”. For some reason I found that text hysterical. I asked her if that was something she wanted to try and she said “If you want to”.
The next day after our morning shift I dropped her off as usual and as usual she invited me inside for a cup of tea. We sat on her sofa and kissed and cuddled and she asked “Do you want to go to upstairs?” I smiled and took her hand led her to the bedroom. She pulled down her blind and closed the curtains and we undressed each other as usual. I kissed her neck and pulled off her jumper, I then kissed her shoulders and undid her bra letting those beauties just fall out. I liked to bury my face in them while I undid her pants and helped her step out of them.
“Diana you are so hot” I told her as she helped undress me. She never responded to comments like that other than saying thank you. She did like to touch my body; she would run her hands over me. I was 23 6’3 and broad. She liked how I felt I think and I knew she was turned on by a younger man desiring her so although she didn’t like to say it out loud.
“Can I titfuck you Diana?” I wanted to be direct so I asked her straight out.
“Yes..” She said, it seemed like it was hard for her to admit. She found it hard to admit she wanted things sexually.
“Do you want me to?” I asked
“Yes David” Diana said, she never called me Dave, always David. Diana went over to the side of the bed and pulled out a towel and a bottle of baby oil. She lay the towel on the bed and climbed on it. “I’m ready” she said.
I laughed and climbed into the bed next to her I took the bottle of baby oil off her and said not yet.
“Let me make you feel good first” I told her. I kissed and kissed down over her breasts and nipples. I sucked them while I moved my fingers to her pussy which she had started to shave for me. I slid my fingers inside her and felt how wet she was.
“David…that feels nice…mmm” she was a very police moaner. I liked to tease her.
“Do you like my fingers in you” I whispered in her ear
“Mmm yes” she moaned
“Do they feel good”
“Ohhh yes” Diana whispered I felt her hips moving with my fingers inside her.
“Do you want me to lick your pussy?” I loved teasing her like this
“Mmmhmmm”
“You have to say it Diana” I pulled my fingers out of her and rubbed her clit with my finger tips. I wanted her to stop being so shy and enjoy herself.
“Please David, lick my pussy” I smiled and moved down her body and licked her thighs before flicking my tongue across her clit, I would kiss it and suck on it. I pushed my tongue deep inside her and she moaned and writhed on the bed “Oh David please, oh David mmmmmm” she would say. I could feel her legs shaking when I hit the right spot. So kept going until her moans became shouts and she cried out “Oh God…. David, Oh Good ughhhhmmm” She arched her back as she came while I licked her clit as fast as I could.
“Did you enjoy that?” I said
“David you are so naughty” Diana replied breathing heavily. I climbed over her and straddled her chest.
“I’m going to fuck your big tits now Diana” I told her, I poured some baby oil on her breasts and told her to rub it around and I poured a little on my cock as well. She looked up at me as I placed my 8inches between her boobs. “Squeeze them together” I told her. She pushed her huge breasts around my cock and I put my hands on hers so we were holding her tits together. I started to thrust slowly in and out between her breasts. They were so soft and warm, I’ve never had so perfect a titfuck in my life. I played with her nipples as I fucked her tits.
“Does that feel good?” Diana asked.
“It feels fucking amazing, I love your tits” I said, I started to speed up, I moaned and grunted and told her how hot she was, how amazing this felt. “I love it I love your big tits Diana” I pulled her nipples hard and she moaned. “Squeeze them harder” I commanded, she squeezed them together harder enveloping my cock and I kept fucking them.
“mmmm David” she cooed, I think she was enjoying this more than she thought.
“I am gonna cum Diana” I said, I could feel I was close. “Can I cum on you?”
“Yes” she replied “you can do it on me”
I grunted and cried out “I’m cumming I’m cumming” I tried to pull back in time but not fast enough so my cum shot all over her breasts and neck and her chin.
“Oh David” Diana laughed, she used the towel to wipe her chin and neck but she rubbed her breasts together rubbing my cum all over them. I lay down next to her.
“Thank you, that was amazing” I told her. I felt like I was emptied out. “What did you think?”
“I didn’t expect you to cum so much” she laughed. “That was more exciting than I pictured, I would do that again” she put her am around me. “I am glad I made you happy”
I hope you enjoyed reading about her first ever titfuck. I am happy to share other stories, if you wanted the story of the first time she sucked my cock, her first anal or anything let me. As always feel free to message me or AMA.
Source: reddit.com/r/sexystories/comments/sfkkuj/mf_my_first_experience_with_an_older_woman_m23