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My first experience with an older woman
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About 3 years ago I was scrolling tinder one night. I have Always been attracted to older women so I decided to change my preferences to above 40 years old. Shortly after a few swipes, to my surprise, I got a match. It was a profile with almost no pictures besides one body photo and a picture of a cat cartoon with the name kitty. Skeptical, I didn’t message but within 5 minutes I had a message in my inbox from this profile.

After talking with her for about an hour I found out she was a married woman in the middle of a divorce and she didn’t want people to find out. We hit it off pretty well and I asked her to go get drinks at a loca bar that Friday night.

Friday night rolled around and I’m sitting there nervously waiting on her arrival until I feel a tap on my shoulder. I turn around and there she is, about 5’3, brunette wearing a tight long sleeve shirt and a pair of jeans that accentuated her wide hips. She had a pretty smile and bright green eyes and I was immediately attracted to her. I bought her a drink and we got to chatting. We got along well, we shared a similar taste in music and she had a great sense of humor. For one of our drinks I got two quarters back and I jokingly gave it to her and told her to flip it. If I guessed right, she had to let me kiss her. She laughed and flipped it, holding it in her hand for me to guess. I called heads and it turned out to be tails.

She jokingly said “well I guess the night is over” and got up from the bar. When she turned back around I grabbed her by the waist and kissed her anyways. After a long kiss she said “hey, that’s cheating” to which I replied “did you mind?” She told me no and said let’s play again. I joked about what was at stake this time. She whispered in my ear “I’ll suck your cock in my car if you guess right”

Immediately I felt the blood rush to my cock, she flipped the coin and of course, pun intended, I guessed heads. She peaked in between her hands really coy about it, and then grabbed me by the hand and started leading me out of the bar. When we got to her suv I pushed her up against the side of it and we started making out before she opened up the back door and we both climbed In. Immediately she started stroking my cock over my jeans and started to unbutton them. I awkwardly half stood in her car and pulled them down, my cock springing out of my jeans and almost hitting her in the face.

We both laughed until she took my cock in her hand and started looking at me while stroking it. She then started to lick the tip with her tongue, teasing me before finally taking it in her mouth. I was so turned on that I could tell I wouldn’t last long. She started to take more in her mouth and bob her head up and down faster before pulling it out of her mouth and taking her shirt off. She had surprisingly perky tits for an older woman and she let me get a good look as she stroked my cock and looked at me before returning to sucking my cock.

I was already close, and I told her to keep going and I was going to cum. This lit a fire in her and she sucked it voraciously. Bobbing her head up and down and gagging on it until I couldn’t help it anymore. I managed to gasp out an “I’m gonna cum” before I started. She helped the tip of my cock in her mouth and stroked the base as I came, shooting rope after rope of cum into her mouth. Small amounts of it beginning to leak out of her mouth onto the shaft of my cock. As my orgasm finally ended she swallowed what was in her mouth and held my cock and began to lick off what was on the shaft.

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4 months ago