Best Sex with an Older Woman

Story Info
Best head of my life.
1.3k words
4.07
26.8k
10

Part 1 of the 2 part series

Updated 12/13/2023
Created 10/11/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Dimmo
Dimmo
3 Followers

My best from an older lover.

I had met Heather some 30 years earlier and we had been sexually involved for a few months. She was 43 and long-time divorced and she was a very horny girl with long blond (dyed) hair down to her bum. She was quite attractive and had a girl next door appeal. She was a redhead and had sparse red pubes on a gorgeous slim body. Her boobs were C cup and stood proud on their own. As she had not had any kids, she was very trim with a taut tummy and a naturally small pussy with what she calls meaty bite inner lips and sparse hair trim. Lovely to nibble on and look at. They are hiding a small but very sensitive clitoris.

I was 37 and had split from my ex-partner at the time. I was about 178 Cm and 82 Kg, reasonably slim and fit with average to good looks. Just out of the Army so relatively fit still. My cock is just under six inches, a bit thicker than average and seems to do the job well. I also shaved the whole area covered by boxer shorts. So pubic / anal and bum cheeks etc. Started doing this to help avoid eczema rash down there and loved the feeling with no hair so continue to be smooth this day.

I was working full time and lived a fair distance 80km from her town, so our time was a bit limited. We saw each other for a few months until I decided to try and sort things out with my ex-partner. After this we had minimal contact for many years. My ex and I split again, and I moved towns and jobs, remarried (big mistake) etc. but still occasional phone contact with an occasional visit. No sex though.

So, thirty years after meeting Heather (she is now 74 and me 68), I end up divorced again and trying to set myself up for retirement ie. Buying a house, setting up the yard, building a shed etc. I had met another lady I was seeing for friendship and sex which was working quite well no strings and good company.

Heather had been calling weekly to keep tabs on me and told me about her car troubles and how her nephew had not fixed it. I said I would have a look so I did. Replaced radiator then found other problems. Anyway, we went in for a coffee and I was looking at her DVD player to set it up and was on all fours when she felt my package from behind. I did not pursue it further then but chatting on the phone later she told me she remembers every detail of our years old sexcapades and was very horny and had not had sex for more than twelve years. I was also told masturbation was not working for her anymore, reason unknown but possibly linked to medication.

Next time I went over to do some work on the car she was suggesting what she would like to do. As we went in for a coffee, she stopped suddenly in front of me so I grabbed hold of her so I didn't knock her over and my hands landed on her now low hanging boobs. Naturally I started tweaking her nipples and massaging he breasts. She started groaning and telling me I was naughty but did not tell me to stop and I did not go further.

The chat on the phone became more direct about her response to nipple tweaking and thinking about what we used to do. I was told of her problem with incontinence which was why she had not gone further on our last meeting.

I had put some pictures and a video on her computer for her which she loved but she really wanted to get hold of what was in the pictures. I was told the video of me cumming was a waste as she wanted me to save it and let her suck it from me.

Next trip over to her place I did a bit on the car while she made comments about my bum leaning over the front of the car. Inside later after having replaced her waterbed bladder we were having a coffee and chatting, she said she wanted a cuddle so with her standing against the sink I moved to her and embraced her, and she then softly said she still loved me and wanted me. I started moving my hips against her and got the your being naughty again and I started thinking she wants to start something. I was getting very tight in my jeans when I left that day and thinking I could explore a lot more next time.

My next trip over was to remove parts from the car to get part numbers and be machined. We were then just chatting with me about to leave when a kiss was asked for. As I was kissing her, she said do you want to come into my bed. I said if you are sure and she led me into her room. I undressed and she took off her trackky daks but left her t shirt on and got into bed. Cuddles ensued then I started down to eat her sweet little pussy. After a time, she told me it wasn't going to work, possibly due to no buildup with foreplay so back to cuddling. Then she rolled over me and began stroking my cock and teasing my balls. Then licking up and down the shaft and taking my whole length in her mouth.

What followed was heavenly, with her using a gobbling action that really stimulates as well as taking my whole length into her mouth. Her other hand was teasing and fondling my balls and slowly moving further back towards my anus. Fortunately, I do take some time to cum so I am able to enjoy this action. I was not sure if she wanted to play with my anus or was just teasing close to it, so I spread my legs wide open and she ran her finger over my hole teasing, I said OH YES, and she continued to tease me there and up to my balls.

Then she wet her finger with saliva and penetrated me with the tip of her finger as well as sucking my cock hard with her lips against my pubic bone. As she wriggled her fingertip inside me, I began the rise to orgasm. She did not stroke my prostate, but her oral skills had me going over the top anyway and she kept her mouth full depth on my shaft and milked me of all I had. She took all my juice and swallowed and kept on sucking until I had deflated. It was the first time I have been sucked to orgasm in the mouth, absolutely heaven not to have the stop start of pull out and finish with wanking, then it was all swallowed and finger removed and then she lay back smiling and said she needed that. Damn did it feel good. The feeling of being fully encased in her mouth was fabulous, similar to pussy but the tongue and lip action was exquisite.

As we chatted after while still laying there, she told me she has always loved suck and swallow, but we had not done that to me previously as she didn't know if I liked that. Also wasn't sure if she could play with me anally. I told her she could pretty much do anything she liked as long as no pain or filth. So next time super oral and a prostate massage she promised if she decides a FWB relationship is possible.

In the meantime, we will work on her and get pussy happy. She is very tight but maybe a lot of oral, teasing and lubrication may result in some lovely penetration as well. My memory of her pussy is a very tight warm glove but now she has scarring internally from a medical procedure so it may not work well for penetration. Time will tell, I guess.

Dimmo
Dimmo
3 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
massageguy1massageguy16 months ago

Blonde or red hair? You contradicted yourself right off the bat

1961Mike1961Mike7 months ago

Please write us more.

nortythortsnortythorts7 months ago

A good first story, I think it would be better if you avoided "etc" and either left the sentence as it was or expanded it with what the etc signifies.

Share this Story

story TAGS

Similar Stories

Teacher's Apartment 18yo discovers the object of his lust lives a few floors up.in Mature
Horny Widower Finds Holiday Cheer Benny seduces middle-aged wife while her husband is at work.in Mature
Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
My Summer with the Church Lady 20-year old stud seduces the fifty-something church lady.in Mature
In Praise of Younger Men He rescues a woman in distress. In more ways than one.in Mature
More Stories