Ashley (Again)



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Arkansas
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 18
How many hookup stories have you here posted before? Several

Ashley (Again)

How long ago did this hookup happen? 42 Days ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? This is the same, beautiful, sexy, amazing woman from my last submission.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? By this time, we had moved past a FWB scenario and had developed real, significant feelings for one another. There was a real connection that we had felt from the first day we met, but since I am married, we never acknowledged it. We finally stopped fighting it and gave ourselves over to our true feelings. No longer was this just casual sex. There was passion and sensuality. We were making love.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She was off work and I had the freedom to adjust my schedule as needed, so we had arranged to meet at her house that afternoon. When I arrived, she had just gotten out of the shower and was wearing only a large, oversized sweatshirt. Damn, she looked good. She is the sexiest woman I have ever met. Fresh out of the shower, no make up, hair pulled up . . . a natural beauty. We had made love just four days ago, but I had been anticipating this all day. When I got there, we skipped the small talk and I pulled her close and we started kissing. My hands were exploring her body and she was receptive to my touch. I undressed and then removed her sweatshirt. Even though I had seen her in the several pictures with which she would tease me and many times in person, every time I saw her naked body was like the first time. Her red hair, hazel eyes, pale, freckled skin was like a artistic masterpiece.

We laid down and continued kissing and touching each other. I had waited all day to be inside her and I couldn’t wait another minute. I rolled on top of her and she spread her legs to welcome me in. As I slid my cock into her warm, wet tight pussy, her brow furled and lips pursed as she let out a passionate gasp. As sexy as she was during her usual day, it failed in comparison to how much sexier she was when she was when she was enjoying my cock. I slowly guided myself in and out of her for a little while. I had braced myself with my arms so I could look at her while I was fucking her. She wrapped her arms around my neck and pulled me down on top of her. As we in full body skin to skin contact, she was softly breathing on my neck, telling me how good my cock felt inside her. I picked up my pace and her breathing increased to match. Suddenly it was like she was holding her breath, so I raised up a bit to find her in full “O-face” mode. A few seconds after, she let out a primal moan and started shaking. She was in full body orgasm. I quickened my pace and soon after, unloaded deep inside her.

She absolutely loved it when I came inside her and I loved the closeness and intimacy that it brought to our love making. I slowed down while my cock was pulsating and she began to squeeze my cock with her pussy. The feeling was super intense. Since I don’t go soft after I cum, I continued. I put her leg on my shoulder which allowed for deeper penetration and picked up the pace. Shortly after, she came again and needed to take a break. I rolled off of her and pulled her close. I loved the feeling of her in my arms, especially in the afterglow of amazing sex.

As we were cuddling, she got a phone call. Her phone was on the night stand next to me, so she leaned over me to answer it. She was kind of in a “doggy style” position, laying over my chest with her perfect ass in the air. While she was on the phone, I was caressing her beautiful ass and then made my way to her pussy, which was slippery from my cum. As she was talking, I started stroking her clit. Her face became flush and her breathing quickened. She was doing everything in her power to keep her composure, but was not being very successful . . . stuttering and stopping mid sentence. Finally, she abruptly said, “Sorry, I’ve got to go” and hung up the phone. She laughed and said, “OK, Fucker” as she straddled me and slid herself down on my cock. Her pussy was so full of my cum that it offered little resistance as she slid herself all the way to the base. She pressed her chest against mine, wrapped her arms around me and began to ride me. She would relax on the way down and squeeze me on the way back up. She had amazing grip and it was an intense sensation. After she road me to yet another orgasm, I had her sit up. She continued to ride me as I caressed her beautiful breasts. She looked so amazing sexy sitting up on my cock. After a few minutes, I repositioned her legs so the could wrap around my waist, I sat up and pulled her close to me. I loved feeling her body against mine. It was the most enveloping feeling of oneness holding her close like that with my cock deep inside her. We rocked back and forth like that until I had another strong orgasm. We just held each other, my cock throbbing deep into her. It had been years since I had felt that type of closeness. I could have stayed in that position forever. Unfortunately, I had to finish my work day, so we cuddled a few moments longer and then I got dressed and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Unfortunately, I think that amazing afternoon brought with it a new perspective on our relationship. I believe she realized that she could only have me occasionally and it was a bit much for her. A few weeks later, she told me that she couldn’t keep going like we were. She wanted me to be hers, but knew my situation wouldn’t be changing anytime soon. I had expressed my desire to end my marriage and be with her, but there are small children involved, which makes it a bit touchy. She understood my position and respected my desire to protect my children, but this had become too emotionally difficult for her to continue. We’re still friends, but she asked me to respect her position and give her space to process her feelings. I miss her terribly and think about her constantly, but I love her enough to respect her wishes. One day I’ll be free to give her all of me. Hopefully she’ll still be available.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

How wanted was this hookup for your partner at the time? Very

To whom did you talk about the hookup? How did they react? No one

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The intimacy, the oneness. Feeling so close, that I never wanted to let go.

What was the WORST thing about this hookup? It was the last time I saw her. We’ve spoken on the phone several times, but everything has changed.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve had casual sex with nearly twenty women, but never have I felt like she made me feel. Never have I fallen in love so deeply, so quickly.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? It’s great

You have a hookup story to share? Submit it here!