My First Cougar's Secret

[Bonus Turn On Tip: Even though this story gets hot and steamy, notice how it is told. Notice how toned down the words are, no smut and filth. Do "vanilla" terms make it less sexy? Older women may offend easily. We are not sluts or hookers, lol, well some of us are. LOL. Treat us like ladies and we will make it very worth your while!]

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My First Cougar's Secret

The truth is, I never set out to lose my virginity to an older woman.

Fed up with women my age, I had just been dumped by another girl who couldn't even tell me why she was breaking up with me. Old school as it might be, I treat women well and was planning to save myself for marriage. I wanted to give that special woman everything including my virginity. Making it worse, I see the jerks and losers with hot girls who won't even give me the time of day.

In the meantime I had burning desires and no one to talk to.

One hot summer night, I ventured on a sex chat site. I struggled to find women there to talk to because their guard was up against all the losers pestering them for quick sex. Why should they think I'm any different?

Out of frustration, I messaged a woman "I suppose you are going to ignore me too." Little did I know how much I would regret that first text. She was patient with me and I found out she was a wonderful person.

Somehow she seemed more real than some of my past real time girlfriends and I felt terrible for the way I approached her. She was not to blame for the crap other women had pulled on me. She said she was 36 and married to a loving man, but her sex life was dead and gone.

After a week or so we exchanged pictures.

I confessed to her I was a virgin and she confessed she was actually 59. We each thought the other would be turned away by this news, but it brought us closer if anything.

We didn't know if we would meet because neither liked the idea of cheating and I was still wanting to save myself for my future spouse.

One thing led to another and before long we were exchanging some hot fun texts. I swear I got to the point that I got hard just hearing the text alert coming from my phone. Soon we were meeting on Skype and my desire for her, to actually be with her physically, became overwhelming. She had an amazing body for her age and I just want to taste her, feel her, massage her.

She taught me a lot over the months.

"Never forget how important it is to create that sexual tension," she said. "Once you have her riding the wave of her own desire for you, keep that tension going as long as possible. Make her wait."

When she turned 60, we had been chatting for several months. She retired and was living in her winter house while her husband stayed at their other home in New York.

"How about you fly down to help me celebrate my birthday." She texted me one day out of the blue. This time the bulge in my pants throbbed with instant desire. My heart caught in my throat as I texted back to her, "Nothing I would enjoy more!

"Fabulous! When can you come (wink wink)" came the text reply

I tried to stay nonchalant, as if getting an invitation to spend a hot weekend with a sexy older woman was something that happened every day. "When is good? I will book a flight." My fingers fumbled with the buttons on my phone as I tried to get Suri to pull up flight info.

The thought of being in her bed intoxicated me. I reached down and held my firm self while I waited for the airline agent to come back to the phone. I wondered what she would be like in person. I was scared partly, what if she didn't like me? What if I disappointed her?

"Sir? Sir?" A female voice interrupted me.

"I have a flight on Thursday at 9 am, will that work for you?"

"Abso-fucking-lutely!" I thought.

"Book it." I said.

We agreed not to have any skype meetings until I got there. Her idea to create even more anticipation than we already had. She told me that women over 50 need a lot of time to feel totally aroused. "If it gets too hard for you," she told me one night, "take care of your own business before we chat. You never want to pressure a woman because you need to come." I loved how honest she was with me.

Somehow I made it through the rest of the week and next thing you know, I was headed toward West Palm. My heart was pounding hard when the pilot announced our arrival. Knowing that she was so close was killing me. Luckily, I had just my backpack and did not have to deal with luggage. As soon as we were on the ground, I turned on my phone.

"Can't wait, baby." Was the text waiting for me "I'll be in front in the black jaguar convertible."

Rushing past people, I hurried to the exit. The minute I got outside, I saw her. She looked beautiful in that car. Big sunglasses and beautiful lipstick on full lips, a hat to protect her from the sun. She got out of the car and walked around to meet me. She had white capri's and a shocking pink wife beater that accentuated her curves. I could barely breathe.

She reached up around my neck and hugged me. "I am so glad you came." She whispered in my ear. Her perfume filled my nose and I melted in her arms.

"Move it along! Move it along!" The security guy said to us, blowing his whistle. I thought I saw a twinkle in his eye.

She put her hand on my thigh and I covered it with mine. We talked about something on the way to her place, but I couldn't tell you what it was. Once we got there, I had to lay down, my head in her lap as she drove into her garage so the neighbors wouldn't see me. As soon as the garage door was closed, she reached for me and I came the second she touched me.

"Don't worry about it." She said. "We have all weekend."

As soon as we were in the house, I picked her up and carried her into her bedroom. She gave herself to me in every way. I didn't feel very confident at first but once we started kissing, fondling and holding each other, she melted into me and let me stroke her and touch her. Because I had come already in the car, I was able to concentrate on her and her pleasure.

She was willing and responsive to my touch. Her orgasm was deep and I felt amazing knowing that it was me that was giving this to her. Her hand was scratching the top of my head as her moans of pure pleasure filled the room. "Yes, yes, please never stop." She whispered hoarsely.

I was young and I stayed hard the whole time I pleasured her. Once her orgasm was over, she gave me a blow job I will never forget. She worked me over like she genuinely cared for me. She told me she had never had a cock as thick as mine. I could feel myself building up, Oh God.

Aching with need I let myself go. She sucked and milked me as I held her hair back so I could see how beautiful she looked.

Everything I hoped for was happening. She looked me right in the eye as she held me in her mouth until I got soft and then she crawled up and snuggled herself against my chest.

She was insatiable and a great coach.

We spent most of the next 3 days exploring each other's fantasies and ordering in food. By the last day, we had christened every room in her new house. She was insatiable and a great coach. She gave me so much confidence in myself and was totally cool about me being inexperienced at first.

I definitely don't regret giving my virginity to her and I can't wait to meet with her again. We both know it will happen soon. You never know what life will throw at you. I never thought I would meet someone from a chat site, let alone with the rude way I introduced myself. I will forever be grateful that she didn't judge me and gave me a chance.

{Bonus Turn On Tip: This kind of story setup can be perfect for a nervous fifty something who is new to Literotica. Sharing this story with a new potential sexmate may inspire her to say yes to role playing something like this with you!! Leave a comment and let me know how it works!]