The time I [32M] lost my Creampie Virginity to a Hot Cougar [47F] [MF]

I wanted to share my first time with one of my best sexual partners – my past FWB Lisa, a hot corporate cougar.

I want to start off the story with the pickup, date, and then sex. But if you are anxious to read the goodie part about sex, you can skip to the part where is says **”The Sex”**.

**The Failed Pickup**

For a few months, I had to take the train to work. It was a long commute that lasted one hour. So I often had a book with me to read. I had to make a transfer to take the route to work.

One such Friday, I distinctively remember it was a December. I boarded the train. It was early in the morning, just before 8am. The train wasn’t packed, but there were no seats. I didn’t mind standing by the doors to read my book.

As I was reading my book, I noticed a pair of hot legs across me. My eyes naturally and immediately went there. A woman was wearing a skirt, and I could see part of her shiny white thighs.

After a few seconds of staring, I decided to check her out. I saw that she was looking at me. We immediately made eye contact.

For a split second, I thought she caught me. But a part of me wanted to continue. In that instant, we both smiled at each other. It was on.

Throughout the next few minutes, we just kept exchanging glances. Because it was a relatively empty car, I could not approach her. We kept this eye contact, smile, looking away charade going on for a bit.

Then after a few minutes, her stop came, which was a stop before mine. I was getting late for work, but I really wanted to make a move, but I froze.

At her stop, she stood up, made eye contact, and left the compartment, and then she looked back. I don’t know why I did this, but I winked at her. She smiled, and she left.

I beat myself for not talking to her. But because I was late for work, I didn’t make a move that day.

I decided to time myself each day, so I could meet her. Unfortunately, for the next 6 months, I did not see her.

**The Pickup**

By this time, I had given up hope. The chance of seeing someone again on the train is slim to none.

Then 6 months, on another Friday morning, I saw her again.

As I walked onto the train, I saw her sitting across. We immediately made eye contact and smiled. She even said “hi”.

Lucky for me the seat next to her was empty. So I approached her and asked if I could sit next to her. We started chatting for the next few stops.

She told me she works in banking and her background. I don’t remember the details of the chat, but it was small talk. Then her stop came. I decided to walk with her. We walked for a bit, decided to meet for coffee.

She lived somewhere central in the city, so it was convenient for both of us. We exchanged numbers and agreed to set up a date. She also told me that she liked the fact that I made eye contact and winked at her a few months earlier.

As we texted, she asked me how old I was. I told her I was 32. She was 47. She asked if I was OK with that. I replied, *”yes,”*. We agreed to meet the following weekend.

**The Date**

I was temporarily living with my folks at that time, and it was on the other end of the city. So I could not take her to my place. So the only option was her place or a hotel.

For logistics purposes, I thought it might be better to have a date close to her home. Plus, that area had an abundance of restaurants and bars. I had no clue how to escalate because I have never been to a girl’s place until this point. Usually, I would invite them over in the past when I had my own apartment.

We meet outside the bar we both knew. We hug each other and decide to get a seat at the bar.

As we approached the table, she asked me to sit next to her. I liked this. I am never a fan of sitting across your date. It feels like an interview. Sitting next to each other is a better setting for a date.

The date was free-flowing. We talked about each other’s backgrounds, careers, past relationships, etc. Then quickly, we started speaking about sex. I liked how free-flowing the conversation was. We both had no hang-ups about talking about culture and sex.

We were talking about our kinks, what we liked. Man, I love cougars; they are confident.

Then she told me “sex without a condom” is so good and feels different.

I told her, *”I’ve never done that. I am afraid of STDs and, more importantly, about getting someone pregnant”.*

We discussed other things as well. We were having a good time.

By now, there was no touching or any type of escalation. She said she wanted to use the washroom and left. I waited there at the table.

I was calculating in my mind what I can do — whether I should take her to a park nearby and escalate. I did not know how to have her invite me to her home. So I decided to take her to the park.

She came back from the restroom and sat next to me. There was an awkward silence and tension. We could both feel it.

I asked, *”What are you thinking?”*. She told me, *”I am wondering how it would feel if we kissed”.*

Without hesitation, I leaned in, and we kissed. It was not a heavy make-out. But still electric.

She smiled after the kiss.

I told her, *”Hey, let’s go to a park nearby and continue this chat”.*

She replied, *”Why don’t you just come over to my place. It’s close”.*

I was taken back. Both were surprised, and I was smiling.

She then said, *”Is that too forward?”*

I replied,*” No. It’s not that. That’s very confident from a woman, and I find that out”.*

We both smiled and acknowledged the vast sexual tension in the air. We settled the bill and then walked to her apartment.

**The Sex**

We entered her apartment. It was a spacious place. There was a giant couch in the living room, and then her bedroom was next to it. She asked if I wanted anything to drink. I said, *”water would be fine”.*

I sat at the couch. She brought the water and sat next to me. I took a few sips of water and placed it on the table.

At this point, the sexual tension was unbearable for each of us to wait. We both pulled each other towards one another and started making out intensely. We sat on my lap and devoured my lips. It turned me on even further.

We kissed and sucked on each other’s necks just enough not to give each other hickeys.

Then she started unbuttoning my shirt. She moved her fingers and hands through my chest and pecs. I was doing a lot of pushups then, so my chest was defined.

As she was running her fingers, she told me how much she liked it. We kept making out more intensely now. Soon her top and my shirt came off. We were kissing each other wildly. I sucked on her boobs and nipples, and she left out lovely long moans, which turned me on even further.

I then told her that we should go to her bedroom. She led me there. We were both topless as we walked into the bedroom. In the bedroom, we started quickly removing each other’s clothes and in a moment were noticed.

I liked her body. She was slim with no fat. But had a soft and nice ass. I have never felt a softer ass like that before. I kept squeezing her butt, and she seemed to enjoy it.

She pushed me on the bed and got on the ground. And she immediately started giving me head. This woman knows how to give head. She didn’t miss an inch or any nook or corner of my dick and my balls. She devoured it. During the blowjob, she kept telling me how much she liked the color, shape, and smell. All this turned me on even further.

Next was my turn. I asked her to get on the bed. I started with kissing her lips, then her neck, slowly working towards her boobs.

I spent some time caressing, fondling, and sucking her breasts. Then I slowly moved my tongue down her body circling her stomach, belly buttons, abdomen, etc.

I would move my lips and tongues through her thighs and not touching the pussy. I wanted to tease her and heighten the tension. I would take my lips closer to her pussy, and then move it towards her thigh and kiss them.

She exclaimed in a moaning voice,*” Oh, you are such a tease; you are torturing me”.*

Then I went for the kill. I liked the texture and smell of the pussy. I did my usual pussy-eating routine. I would start around the labia, the lips, suck on them slow and then move towards the clit.

Then I went for the clit — move up and down. I loved how her body moved when I was eating her, and she would occasionally hold my head. I spent some time on her clit. Then after a while, she asked me to stop. She didn’t cum yet.

She wanted me inside.

I slid on a condom and started in the missionary position. I really liked how wet the pussy was and how it slid in nicely. We started with some really slow thrusts back and forth. Then we tried many positions. After doing this for a while, she asked me to come from behind, aka doggy style.

She turned over, and then I entered her. I loved pounding slow at first and then picked up the pace. I liked to also slap and squeeze those milky white thighs. She started playing with her clit. Occasionally I would pull her hair and continue pounding. We did this for a while until she came hard. When she came, she shuddered, and her entire body moved like a snake. It was so hot.

We continued this for about an hour. Then we decided to take a break. We both went to the bathroom, drank some water. Then we just laid in bed and talked about stuff – -work, life, dating, etc. After maybe another 30 minutes, we were gently touching each other, and we were getting turned on again.

We started making out hard. She lifted her butt, guiding me to do the doggy style again. I took off another condom from my pants. Put it in and slid it in her. I was starting slow again.

At this point, she said “*If you want to take the condom off, you can do it.”*

She knew I have never done this before.

She said, *”Trust me, you will enjoy it better”.*

I made a few milli-seconds conversation in my head. The chances of her getting pregnant is slim to none. She told me earlier she doesn’t want any more kids. And I thought about diseases. Given her lifestyle, I didn’t see her as a risk.

So I did what any horny guy in a room with a hot woman would do irrationally. I threw off the condom.

I put on some spit on my cock, and slowly entered her. Oh gosh, it was terrific. Yes, she was right. It’s totally different. The sensations were different.

We continued to go at this position for a few more minutes. Then I could feel I was going to cum. I slowed down and asked her where she wanted it. She pushed her butt back into my dick and told me, *”put it in me. I want to feel it”.*

I lost control when she said that, and I immediately came. It was one of my biggest loads.

After cumming I fell on the bed exhausted. She looked at me, smiled, and said, *”that was a lot; you seemed to have a lot of cum saved up in you”. LOL.*

She was right. At that point, I was on NoFap and had not jerked off for more than 30 days.

We then spoke for a bit. She asked if I wanted to stay over. I decided not to stay. Not because of her, but I had a breakfast meeting with a friend. So I said goodbye, called an UBER, and headed home.

That same week, I also rushed and got tested. Everything was fine. I just needed to be sure. I know some of you are thinking that’s irresponsible. But I believe losing my creampie virginity to a hot cougar like Lisa was totally worth it.

Since then, I have hooked up many times with Lisa. Each time was like a new sexual adventure. She got me hooked to bareback sex and creampies. A few years later, we had a steady FWB situation, and I had one of the hottest sex with her.

If you guys liked this story, I would share more of my sexual adventures with Lisa.

Source: reddit.com/r/gonewildstories/comments/n22z3k/the_time_i_32m_lost_my_creampie_virginity_to_a