by Kimberly

Gender: Female
Age: 22
Race/ethnicity: Asian American
Current location: Southern California
Highest education received: Some college (currently in college)
Occupation: Key Holder
Relationship status: Single
Religious affiliation: Buddhist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 0

My Ex Boss That I Let Manage Me Till Now

How long ago did this hookup happen? Yesterday

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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? He is tall, blue eyed, brown haired, athletic build, 1/4 Chinese and 3/4 Caucasian. I know enough about him to agree to hang out with him, but not too well. This guy was previously my boss, at a fast casual food restaurant. I was his employee for only two weeks before I decided to quit. I felt very timid, and highly attracted to him, I mean the moment I met him I was instantly attracted to him. Upon meeting his estranged girlfriend, I thought “wow she’s lucky”. He’s is undeniably hot, and to be frank I was having trouble working for him. As I went to pickup my last paycheck, I felt his eyes on my but did not want to mistake it for flirting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began in his bedroom as I somehow I went from sitting in my own chair to me on his lap as he began to softly kiss me. I am infatuated with The Weeknd and Drakes music so the topic of discussion consisted of that and music listening and streaming YouTube. Very little planing was involved, we had agreed on getting a drink. Once I got in his car he proposed we go drink at his house while I am struggling on a response back. I felt his sharp flirtatious eyes on me the whole time, and he was pending on me to agree with the underlying knowledge that we were going to hookup. Anxiously I agreed to his proposal as we headed to his place. He instigated the hang out, he initially asked me to hang out last week and I politely declined. Then he brought me food at work to my new place which I thought was nice of him. His piercing eyes on my again while he asked me for a hug as he checked me out in my heels and dress. Called me classy which I am and said he’d text me.

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? From the chair he carried me to the bed where he lay on top of me as we made out passionately. I am self conscious about my body so I was hesitant but he persisted on lifting up my shirt and he began to suck on my areolas. He said to not be embarrassed cause he liked my “small titties”. Then he grab both of hands and held them above my head as he began to insert his fingers inside of me. Usually I am able to push away but he knew his game and felt me as I was wet for him. I felt an amazing rush through my body between my legs, and then he took
his fingers out of me and licked them to taste me. I then began to get on top of him and unbuckle his belt and jeans. Prompting him to turn me over and remove my jeans, and thong. Then he began to kiss between my legs as I held on to his head in motion. I hadn’t shaved but all I could focus on is how amazing his tongue felt in me and his occasional finger inserting me and out. He somehow got undressed and after he began to rub his dick against me and he then inserted himself inside of me. I immediately shrieked out in pain, but a good sensual pain. We were in missionary and then I rode him as I moaned and groaned. Then he flipped me around and rode my ass from behind so hard and good that I screamed. I sucked him as he choked me, then we did it again.  But this time he had me wear a princess crown and I asked him to slap me, which he did. He inserted his fingers in my anus stimulating arousal contributing the my cliterous. I was baring all which is rare, and we just lay their after cuddling as he kissed me and told me he had a good time. He held my hand and we fell asleep. I woke up concerned about what time it was and I asked him to take me home and he insisted I stay the night. Attempted to fall back asleep and couldn’t with the thought that I needed to return to my own bed. So as I bugged him again, he reached over and touched between my legs again and he got up and inserted me again. It hurt so good, I wanted to cry all three rounds. On our way home he held my hand briefly and before I got out of the car I demanded he get out and hug me. All that was on my mind was how great of a lover he was. We kissed a few times as he squeezed my butt and we said good night.

Did you have an orgasm? Did your partner(s)? I know he orgasmed; three times, on me and beside me. I believe I orgasmed after the first time when he rode me. My last partner did not ever please me or handle me the way this guy did. It was roughly passionate and kinky, just how I secretly desire.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Unfortunately we failed to take all the necessary precautions to prevent std’s and pregnancies. We did not discuss STI history, I did not want to spoil our night. However when the opportunity arises, I will inquire.

What were your REASONS for having this hookup? A few of the reasons for having this hook up 1. I am sexually very attracted to him 2. I was very horny 3. Wanted to full-fill my secret desire of being with my hot and sexy ex boss. It went further than I was hoping, however I am glad he was very aggressive. I could not resist himself nor was he going to allow me to.

Were alcohol or drugs involved? If so, how much? Alcohol was involved, we took a few shots of Absolute hibiscus vodka that got me tipsy. He has some shots and a beer, but he was just as tipsy as I.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After the hookup I went home feeling very sore, satisfied, hungry, and yearning for him inside me again. My expectations/hopes for the future with this person to continue just being cordial. We agreed that this is going to be our secret. My now manager is a female that I had met during the time I worked with my ex boss. He had intentions to hang out with her but she declined. All of my assumptions about him are have been confirmed. Charming yes, always, good in bed, kinky, and sexy, yes. I do not want this to become a habit since things can get messy and I also do not want my now manager to know about my rendezvous with my ex boss.

To whom did you talk about the hookup? How did they react? I spoke about this hook up to a few of my girlfriends. I couldn’t wait to tell them about my rendezvous with my sexy ex boss. One friend condoned me since he is so attractive and another friend was shocked.

Was this a consensual and/or wanted experience for you? For your partner? This was very consensual between him and I. It was very wanted, the moment I accepted his invitation. The moment I agreed to his proposal of a hang out in his car we knew we were going to hook up. I was so nervous as he was just sitting their eyes sharp and confident.

Do you regret this hookup? If so, why? I do not regret this hook up, however intercourse was not my intention.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hookup is satisfying my fantasy of getting with my ex boss that I am highly attracted to. It his piercing blue eyes, to his charming personality that I can’t help but get aroused to. This hookup has not changed the way I think about casual sex, my story is one of the many examples of casual sex. This hookup has confirmed my fondness of my weakness for charming player types.

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

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

Anything else you want to add about this hookup or anything else? It was the spur of the moment act, I don’t necessarily condone casual sex. However if you are attracted to the opposite sex or same sex in front of you, go for it. We are only humans with natural hormones so if it feels right, trust your judgement. If you do not feel entirely comfortable, dismiss yourself from this situation immediately.

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