her 1st orgasm to pillow princess Part 2 [MF]

Part 2

Over the next couple of days we talked about it. She asked if she really tasted any differently than other women or if I was just saying that. I assured her that she was especially delicious. She told me how much she enjoyed her smooth pussy now and wondered why she had never done it before. She said she had masturbated a few times in the days after, but couldn’t make herself cum. 

A few days later I was invited back. This time the dog was not locked up. Jen was fully dressed. We chatted a bit. This was the awkward part we avoided the first time. Then there was a pause in the conversation and we locked eyes. Started kissing. Laid on the bed and started removing each other’s clothing. Mollie jumped on the bed and tried to get in on the action. Jen finally got frustrated with her and put her in the closet. 

I forgot to mention that on the first time, Mollie barked a lot. It seems Jen was used to it as she came just fine. It took me a little effort to block it out. Jen said she thought maybe leaving Mollie out of the closet would stop her from barking. But it didn’t. So back to the closet for Mollie. 

We were both totally naked and making out. She was stroking and fondling me. I suggested she just relax and not expect that just because she came so easily the first time, that she would cum at all this time. 

Wow, I was wrong. I skipped some of the all-over body kissing and prolonged build up this time. But similarly teased her pussy before diving in. And she came so quickly. This time I decided to see if multiple orgasms would be possible. After she came from my sucking and flicking her tongue, I again cleaned her up. Fuck she tasted great. 

Then I put my middle finger inside her and curled it up toward me to stimulate her g-spot. Fuck, that worked almost immediately. 

“Fuck me! Fuck me now,” she said. 

I explained to her that I was serious about not fucking anyone. She asked if I didn’t want to cum. I told her I would love her to give me a blow job. She said she hated giving blow jobs and had previous bad experiences. But she really wanted to fuck me. I suggested we settle on a hand job. She was really bad at giving a hand job. 

As turned on as I was, I figured any friction would have me cumming quickly. She was hard and not rhythmic and just plain awkward at it. I asked if I could straddle her and cum on her tits. She agreed. 

As the semester went on, we would meet up pretty regularly. Sometimes multiple times a week. I would go down on her. Got her to ride my face. The first time she rode my face she realized that she was looking straight into an entire apartment building across the street. Her bed’s headboard was against a window. 

She wanted to get off my face or stop to close the curtains but I told her it was so hot to think of people watching her orgasm. And that if she closed the curtains I would stop and go home. That must’ve really turned her on because she came quickly, and hard. 

It was fun. I do love eating pussy. But I also was a bit annoyed that I put so much effort into her pleasure and she wouldn’t even try to blow me. I really liked eating pussy (as if I haven’t said that enough times already), and would totally be up for going down on a woman without reciprocation again sometime. It just wasn’t working for me after a while with her. It came across as selfish. I never pressured her about it, but I would ask sometimes. I would sometimes hide from her on AIM, or tell her I was busy when she IM’d me. Our get-togethers got a little less frequent. 

I was fooling around with other people. And none of them had the same qualms about a blow job. One girl I met online lived not far away. She liked to give me a blow job, then have me watch her use her vibrator on herself, which would make me hard again, and then blow me again. She was cool with the no sex thing and didn’t even want me to do anying to her. 

In addition to the ex issue, i decided that sex drove too much of my life’s decisions and it was a good idea to take a break for a few months. It occurred to me that I had used sex as a way to validate my self worth. If a woman would give herself to me, then I had to have value as a human. Even if that woman was not someone I much liked or respected. 

So even after it seemed clear the ex and I would not be getting back together, I decided no sex. Of course, in my weird logic that just meant no penis in vagina. As I look back, I was still slutty and spending lots of time looking for women to hook up with. It still was a sense of false validation. So a mostly failed experiment. 

I was also surprised by how many women got angry that I wouldn’t fuck them. I was very generous with my mouth and successful in bringing them to orgasm. As I look back, it was probably them seeking their own validation and feeling rejected when offering their bodies. But I was always clear before things got out of hand that I would not be having sex. 

Anyway, back to the story. 

My ex asked me to be her date over spring break to her dad’s wedding. I agreed. I liked her. We were still friends. I just didn’t see us getting married. We shared a hotel room, but I had no expectations of anything happening. She picked me up at the airport and on the way to the hotel she asked if I had had sex with anyone during our break up. I assured her I had not. She also said she had not told her family about our break up. She assumed it would be temporary. So she asked me to play along. 

We got to the hotel that afternoon and she immediately jumped me. We had maybe the best sex we had ever had. But then lying there naked she did something she never should have done. She asked if I thought we would get back together. I honestly told her, “no.” 

She should have saved that question for the drive back to the airport. It was awkward at times over the weekend, but we did have good sex a few more times. 

Jen was IMing me while I was at the airport. And it came out that I had now had sex. I told her that she had asked for it multiple times, so now that I was having sex again, she could be the first (not counting the ex). She seemed to really like the idea. 

I went straight to Jen’s from the airport. 

Turns out, our sex was not good. She only seemed to like me on top pounding her as hard as possible. I liked a little more variety in pace and position. She never came from penetration with me. Not sure why she liked that style of sex as it had never given her an orgasm with anyone.

The spring weather was nice and her curtains and windows were open. I got her to get on top and ride me. The only time she ever did. She looked so damned sexy and I kept telling her that people were watching her and getting turned on by how sexy she looked. She seemed to like that. I certainly did as that’s about when I came. 

We hooked up a couple more times before the school year ended in May. It was usually just me giving her an orgasm orally and then not great sex until I came, or me going home to jerk off. I actually missed the days of no sex and me jerking off on her tits or pussy to finish. 

The school she went to was not very highly ranked and she had applied to transfer to a number of more prestigious schools. While I was back home during the summer for an internship, she found out she was accepted to a good school back in the South and she moved before I got back to town. 

I never saw her again. We stayed friends for a few years on AIM, then social media, occasional phone sex, once was hot when told me she wanted to pull over to the side of the freeway and cum for her right in the car. 

She did learn how to give herself an orgasm. She also tried waxing and told me she wished she had tried it sooner. I do, too. She also found a guy who could get her to cum. Then she and the guy got into some really kinky stuff. He liked her to ride his face and then pee in his mouth. No kink shaming from me. Not my thing, but it worked for them.

She thanked me many times for opening her up to different sexual experiences and helping her learn to cum. She even apologized a few times for never even trying to blow me. She told me a story about some guy pretty much sexually assaulting her in college by painfully throatfucking her. But she said she should have still tried with me. 

I told her I really enjoyed our time together and that she really did have one of the best tasting pussies ever. She said subsequent guys had agreed about her taste, so she finally believed me. 

Source: reddit.com/r/gonewildstories/comments/xftgro/her_1st_orgasm_to_pillow_princess_part_2_mf

1 comment

  1. I appreciate the end of the story and knowing where things went, even if this wasn’t a “hot” story.

    It really sounds like Jen was bad at everything about sex, possibly from being victimized. Kinda sad.

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