by John

Gender: Male
Age: 29
Race/ethnicity: White
Current location: Oregon
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Business Owner
Relationship status: Seeing Someone Casually
Religious affiliation: Christian
How religious are you? A little
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? One

Blonde Ambition

How long ago did this hookup happen? Ten Months

How would you best classify this hookup? Fuck Buddies/Casual Relationship

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? Jen is a tall, fit avid jogger (what can I say, I like the athletic type). She has short blonde hair and a nice pair of C cups. She also has a tattoo of a rose on her right shoulder I always kind of liked.  She is also a few years older than me and in her early thirties.  I first met her almost three years ago, she started working for my client roughly the same time I took them on.  I will admit I was very attracted to her when we first met but I was seriously involved with someone at the time so nothing happened between us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months prior to my hookup with Jen I went through a painful breakup with a woman I had been seeing for almost three years and was deeply in love with.  I spent a few months hating women and not really seeing anyone, only had a one night stand during this time.
I was at the office where Pam was working and noticed she had on a tight fitting sleeveless top and pants.  She leaned over at one point and made sure I got a good look down her blouse at her breasts.  There had always been an attraction between us but we were both in a position where something could happen.  We had drinks that night and flirted a bit and touched but didn’t hook up even though we both wanted to.  Jen was also dealing with a breakup.  We also had dinner a few nights later.  
She invited me to go with her and a few friends to the lake for the day and I went.  Pam came out in a black and somewhat revealing see through black string bikini and I learned she had a bunch more tattoos.  I got hard just looking at her. She had her son with her so her focus for much of the day was on him but we did manage to steal some time away and we kissed some and felt each other up a bit and her bikini slipped and showed her nipples a few times.  
She sent her son home with friends and we ended up going back to her place since I have a roommate.

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 had on just a pair of shorts and her bikini. We ended up on her couch making out and I took her bikini top off and licked and sucked her breasts.  She started moaning pretty loud and orgasmed from this, only woman I have ever seen have a breast orgasm.  She then pulled my shorts down and pleasured me orally and I came in her mouth.  We cuddled for a bit on the couch before going to her bedroom where we fucked again, this time in just standard missionary and I finished inside her and we fell asleep after.
In the morning we fucked a third time, this time Jen wanted me to take her in doggie style.  I did, and she orgasmed and I did not which for me was a little embarrassing.  We showered together and I then left for home.

Did you have an orgasm? Did your partner(s)? Several times each.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t use protection, but we discussed it briefly and both had recently tested clean and Jen was on birth control

What were your REASONS for having this hookup? Lust and Jen was someone I had been attracted to for years

Were alcohol or drugs involved? If so, how much? A Mikes Hard Lemonade each at her place, but we would have hooked up either way

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? Jen and I have been casually seeing each other ever since.  We go to the movies when we want, go to dinner when we feel like it, and fuck when we want which is quite a lot actually.  We have kept it pretty casual, while I like her and care about her and really enjoy the sex with her I am not in love with her.  
Recently though my ex reentered my life (See Pam).  Complications and the fact I have been hooking up with my ex as well means I am considering breaking things off with Jen (we were never exclusive).  I also think she is sensing that things are coming to an end between us.

To whom did you talk about the hookup? How did they react? My roommate who was pretty impressed, Jen is really hot

Was this a consensual and/or wanted experience for you? For your partner? Yes to both

Do you regret this hookup? If so, why? Not at all

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? Great sex with someone I was very attracted to and the worst part are my worries about how things could be between us after we stop sleeping together.  I felt a lot better about myself and great during this hookup.  This was also my first real hookup relationship, before Jen I only had sex once I was really involved with someone.

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

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

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