A Deadbeat’s Diary – Older Woman who hadn’t been laid in 19 years

It was in the spring of 2005 that I finally met Freda. I say finally, due to the fact that her and I had been chatting online for the previous 3 years before actually having sex. We had met once the year prior but it was for a coffee date that lasted 15 minutes while she was able to get away from her husband at the time.

So here goes my hopefully not too long and complicated true story.

It was the spring of 2002. I was online in the local chat room for a bit of excitement while my girlfriend at the time was working the evening shift. Like many other horny young guys trying to get a bit on the side, I would begin a conversation with ASL – Age-Sex-Location.

So this is how I met Freda. She responded to me by saying she was 42, female and living in a town that was located about 500 miles from where I was living to at the time. She also said she was happily married, had 2 children that were 19 and 25 and that she was not the one who was the cheating type. Yes, We’ve all heard that line before only to find out something else. Luckily for me, I was the one to benefit from this.

Since I was in chats with 10-12 other women online at any given time making progress of various levels if getting my dick wet, I didn’t feel the need to rush things and felt that it would be a long term conquest to fuck her. I was confident that some patience was needed to bag this bird.

Over time we’d chat and due to her being 10 years older then myself, she had taken on a sort of motherly role in my online chats. I would confide in her with my issues and she would help me with them. Over time, she would begin to share with me her problems. She started talking about her husband of 26 years and how there was no love there in their relationship and that at best, they were roommates who stayed together for the kids.

I asked her if she had a webcam and after a week of convincing she agreed to show her face to me online. As I saw her there for the first time, I was attracted to her. I was beginning to really want her. She had short curly hair and was looking a bit older for her age but she had a sexy mile and a sexiness that was hard to explain.

I complimented her on her appearance and she was flattered. She had confessed to me that she was worried that i would stop talking to her since she felt she looked like an old woman and young men didn’t find her attractive.

The next day, she was on cam again but this time had a low cut blouse on exposing what looked like to me 40D tits. I complimented her on her blouse and took a shot in the dark by saying that she was making me feel things I hadn’t felt in so long and that she was a very desirable woman.

Later that night, she surprised me with an email telling me of how I have awakened her sexual being. She also explained to me her story.

She was turning 17 when she had gotten pregnant with her first child. Her and her boyfriend quickly gotten married before the baby was born. Things were going some what well for the next 4-5 years and then she became pregnant with her second son. at the age of 21. During this time she discovered that he was gay. Yes, I said it. somehow the talk of the town she lived in was about how her husband was fucking around with some 17 year old high school boy. She had kicked him out of the room but for the kids, he would still lived there and play Father to them.

She over time became disgusted by sex and anything to do with sex. She burred that part of herself deep down inside of her and worked on being a mother and keeping up a huge lie.

Fast forward to 16 years later and you have a woman who’s sexuality and pussy have been reignited and I was the man who was going to bring her back to life.

Over the next few years, we exchanged erotic pics and had phonesex every chance we had. Problem was that we both had partners and other obligations to worry about and we couldn’t get caught.

But luck was soon on our side when she had to come to the city for business reasons. This required that she would be staying in a few times at one of the local hotels here in town.

So plans were made and more phonesex and pics where exchanged between her and i.

And the day arrived.

We agreed to meet at a local hotel near by my house at 10 in the morning. And when we did meet, it was electric. We went back to her room and we kissed. We held each other and I started to make my moves. She touched my hand and said we have lots of time and there is no need to rush.

So I slowed it down just a little. I walked her over to the bed and we laid on the bed kissing and pressing our bodies against each other. I ran my hands down her back and felt her ass. She was a plump lady of around 225lbs but had a great ass. I brought my hand back up and cupped her left breast. I could tell that she was beginning to warm up. I started to put my hands up under her shirt and felt her breast though just the bra and she began to unbutton her shirt. Then I pulled my shirt off and he held each other, feeling skin on skin, nothing between us above the waist besides her bra and i was able to pull her breast out of her bra and suck on the little light pink nipple. She gasped at how good i was making her feel. I could feel her stroke my hair and i reached back to unclasped her bra. She wiggled out of it and she was nude from the waist up. I pressed my chest against her and we started dry humping each other. Then then pulled her pants down while still intertwined with me but leaving her panties on. Her panties were a dark green high cuts. I felt her ass though the silky material and i was getting so hard.

I pulled my pants off. I wasn’t wearing any underwear so my cock was stuck off and when we got close again, i could feel my cock press into her lower stomach and into the front of her panties. The conbination of silk and lace material stimulated my hard on. I reached my hand down and cupped her pussy over the crotch of her panties for the first time and I could feel so serious heat coming from her.

I could aslo feel pubic hair and the folds of her crack.

With that, she pulled off her panties and I for the first time saw her beautiful sexy pussy for the first time. I also would like to add that i was the very first man to have seen her pussy in over 19 years. When Freda found out about her husband being gay while pregnant, she stopped having sex with him or any other man for 19 years right up to the morning I finally got with her.

So I reached down and I could feel the pubic hair. There was a bit there but it wasn’t a big amount. I then put my finger beyond the lips of her pussy for the first time finding her entry.

What happened next was a pure shock to me. I tried to insert just one finger inside and i was met with resistance. Contrary to what you might have red, the hymen doesn’t go over again if a woman is sexually inactive. The resistance was caused by her opening being closed for so long, it had almost formed a tight barrier. It took quite a bit of gentle pressure to insert just one finger. I had felt virgin pussy and it was nothing like this. I would equate this to putting a finger inside a woman’s asshole who wasn’t totally relaxed or used to anal penetration.

After a few minutes of gently finger fucking her, I got down below her on the bed and ate her out. It was the first time in her life that any man went down on her and she loved it. I made her cum 3 times and I had to take the next step.

I was very very hard and I came back up to her and got over her on my knees. I grabbed my hard cock and teased her a few times. Ran the head up and down her pussy canal. And then I asked her if she was ready and she said “yes, I am ready, I want you inside me.”

So I lined up my thick bellhead to her entry and I pushed. It wouldn’t go in.

I kept pushing, with each time being more firm and on the fourth try, my cock pierced her entry and it went in. It might of been 19 years but that pussy knew cock when it felt it and I could feel her work that cock. I started off slow, I didn’t go in completely the first few strokes, but as i worked up a faster pace, I would go in further. I loved how her ass felt against my balls and I love how she sounded when she was getting fucked. This was making me so horny. I also know that she wasn’t on any birth control since she wasn’t absolutely shore if she was going to have sex due to the fact that she was quite nervous about so many things.

But I wanted to cum in her. I wanted to leave a bit of “ME” in her when she was to go back home the following morning. Even if it met her getting knocked up, it was a chance I was willing to take.

As I felt myself about ready to come, I slowed myself down and asked Freda if I could cum inside of her. She said that she wasn’t sure, what about a possible pregnancy and her being 42 and yada yada yada.

I said that I didn’t care about that and that I wanted to leave a bit of me inside of her to take back with her.

I then said to her that it would mean so much to me if she would take my cum inside of her and whatever happens, happens. She replied that she loved me very much and that she wanted me to give her my seed.

The thought of her wanting me to give her my seed put me over the edge. I came inside of her, and as i was, I screamed out I LUV YOU FREDA and I’m gonna make you big and take my seed.

As my orgasm subsided, I laid next to Freda and we kissed and held each other.

The next day, Freda left to go home. I had gotten news 6 weeks later that she had a positive test for pregnancy and that she had left her husband.

To be continued…

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