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What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Account Director
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 4

A Walk On The Beach

How long ago did this hookup happen? 6 years 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 1 to 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? I knew E for over 2 years before this meeting happened. She was in her early thirties, was married with no kids, had long blonde hair, a very pleasant body, and perky breasts. She was an account manager that worked on my team and had been a direct report for most of the time I knew her. We had become quite friendly and would talk often. She liked to flirt, and I enjoyed it but thought it was just her nature.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had not planned this, but I think she had. We were at a team meeting with about 120 sales and account managers at a very nice hotel with a big sandy beach on the coast. I was one of 5 directors that lead the team of managers and sales reps. It was early March after a very successful year, and we would always go to “spring training” somewhere nice and warm to celebrate the prior year and plan for the new one. My team had a large dinner event, and E mentioned that she wanted to discuss some things when I had time. After dinner, E texted me asking if we could talk. There was a small beach bar at the hotel next to ours that some of the team had discovered, and she asked to meet there. As I was walking to the bar, she was walking back and suggested we walk the other direction on the beach.

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? As we were walking the other way, the beach became less and less populated. Our discussion was work-related, but E was more flirty than normal. E had taken her shoes off and was carrying them. I was in shorts, but I was not prepared to get wet. As we walked, she would “bump” into me pushing me closer to the edge of the water. Finally, I “bumped” her back. Laughing, she suggested we go swimming and revealed that she was wearing a bathing suit under her clothes. It was a one-piece but showed her breasts and ass quite well. The flirting was out of control now, and I was starting to get hard. She noticed this and made a comment asking if I liked what I saw. She talked me into taking my shoes off and walked me into the water about a foot deep. The waves were hitting the bottom of my shorts. She was holding my hand and kept trying to pull me in deeper. Finally, I lost my footing and down we both went. As we stood up, I pulled her close and we started to kiss. Her breasts were firm, and she pressed them hard against my body. We stood in the water making out and exploring her body with my hands. At this point, we were a little more than waist deep, and I felt her hand grip my cock and start to massage it. In response, I start to massage her clit. We continued to swim and kiss and feel each other up for about 10 minutes before making our way back to the beach. E looked around to make sure we were alone, and then she dropped to her knees and freed my cock from my shorts. She started sucking and gave me an amazing blow job. I let her know that I was close, and she looked me straight in the eyes and said, “Cum in my mouth,” and then went right back to sucking. She never broke eye contact as I unloaded in her mouth. She stood up, licked her lips, and told me how good I tasted. We picked up our stuff and began to walk back towards the hotel. We walked slowly and continued to kiss and feel each other up until l start getting hard again. E noticed this and began to massage my cock again. I asked her if she wanted to continue this in the hotel room. She smiled and said to leave my door open.

We separated and entered the hotel from different entrances. I made it to my room, and she showed up about 10 minutes later. We made out some more and removed our clothes. We showered quickly to get the salt and sand off us and returned to the bed. E was much more forceful then I expected. She started stroking and sucking me to get me hard and turned to a 69 position. She clearly wanted me to give her oral, so I flipped her over and started to go down on her. She gripped my hair and wrapped one leg around my back. E was very direct on what she wanted. She liked being licked gently but not sucked. As she was getting close, she told me to put my finger in her, and she pushed my head down hard onto her clit. Her body began to shake, and she let out these soft grunts before pushing my head away. E grabbed my hand and held it inside her as she closed her legs tightly together. Once her orgasm passed, she rolled over to face me, and we started to kiss. She began stroking me, and we talked a bit while I got hard. E climbed on top of me and started to grind on my cock. Her pussy was super wet, and her tits were very firm. I noticed the scar from breast implants, but they looked amazing. She raised up a little and positioned my cock to slide inside her. The thought about using a condom crossed my mind, but as her pussy slid down around me, I decided to simply enjoy It. She rocked back and forth slowly on me, grinding my cock deep inside her. I was enjoying the view and caressing her breasts softly. She took my hands and pressed them hard against her breasts and asked if I liked them. Leaning down, she positioned them where I could suck on them a bit. The pace picked up, and she rode me quite hard. She was really getting close, but the bed was a bit noisy, so we decided to move to the couch. As she got off me, she took a quick suck of my cock and then kissed me. She took up a position on the couch with her ass facing out and her arms on the back of the couch. She looked back and smiled. I slid in her and grabbed her hips as I went in. As we fucked, she was again very direct. She liked it hard, wanted her hair pulled, breasts squeezed, and liked being bent back a bit. She was very flexible, and it wasn’t long before I was ready to cum. I told her I was close and all she said was “keep going.” I unloaded in her, and she pushed back hard. She started to quiver a little but nothing like before. I pulled out, and we both sat on the couch and cuddled up a bit. I asked her if she was satisfied. She smiled and said, “Oh yes… well mostly.” When I asked what she meant by “mostly,” she smiled and said, “We will talk more tomorrow.”

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? E left my room and headed back to hers. The following day, we acted as normal. I was praying that she wouldn’t say anything or make an issue of it. We were both married, and I was technically her boss. This could go very badly but it was also super exciting. Later that day, we had a chance to talk a bit when no one was around, and I asked how she was feeling. She smiled and said she felt like taking a swim again soon. Nothing happened that night, and we left the following day. However, she asked me to help her with an account meeting a few weeks later. She said she felt the account needed some “executive attention” and that the hotel there “has a great pool.” We spent 3 nights on that account trip, and I provided hours of attention to the account. But that’s another story.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Just happened, I don’t know why, just went along with it

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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

Did your partner(s) consent to this hookup? They gave enthusiastic consent

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? E is an amazing beauty, has a great body, and a wild and fun fuck!

What was the WORST thing about this hookup? She would have made my life very difficult.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Love it

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