by Zev

Gender: Male
Age: 43
Race/ethnicity: White
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Business
Relationship status: Casually Seeing someone
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? This is my first

A “Hard” Time

How long ago did this hookup happen? A Month

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…)? 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? I first met Althea (not really her name) a little over two years ago when she came to see an apartment in my building (I own the building I live in).  She is 22 year old college student, more than twenty years my junior, with very dark skin and long black hair.  She also is short, just a little taller than five feet and curvy with big breasts.  When I first met her I thought she was pretty cute and she struck me as quite intelligent but could never afford an apartment in my building.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I should share a little background of my relationship with Althea. I first met her shortly after my last divorce and started sleeping with her right after that.  I was thrilled and enjoy bedding a much younger woman. I’ll admit to being her sugar daddy, I pay for her apartment and clothes, jewelry etc and in exchange I get the company of a gorgeous intelligent woman and some great sex.  It’s common in my world, most of the men I work with have much younger wives or girlfriends (I work closely with a lesbian and her girlfriend is much younger as well) some of them are married to other people.  For me though such a relationship was a new thing.
As I said though Althea and I have been sleeping together a while now.  I hadn’t seen her in about six weeks, I had been in Europe for work.  I was tired and jet lagged and a bit stressed, it hadn’t been a great business trip but still was looking forward to hooking up with Althea.  I made a light dinner and she came to my place, in a tight shirt and jeans, we kissed and we ate dinner.  After that we settled into watch a movie, just a quiet night in.

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? About half an hour into the movie Althea and I were sitting close and I decided to make a move.  I had been feeling her up a bit, and reached down and unbuttoned her pants and unzipped them and began to finger her clitoris.  I did this to her once in a movie theater, and since then it has always really gotten her going.  It took about fifteen minutes, but I could tell Althea was really turned on and close to climax.  Unlike most women I have been with I can tell when Althea is getting close and having an orgasm, she gets really sweaty and starts breathing heavily and moans loudly.  She was doing all of these and she had an orgasm, and I kept fingering her until Althea stopped me.  It gives me quite a thrill to pleasure her and get her off.
Althea needed a few minutes to recover, she usually does post-orgasm.  She went into the bathroom, and I was really looking forward to what was coming next.  She emerged in only a pink lace bra and panties set I had bought her and was wearing a perfume I had given her.  She straddled me and we made out a bit.  I took her bra off and sucked on her breasts some.
Now this next part is a bit embarrassing for me.  We were both completely naked at this point but I was still pretty limp.  Althea tried some manual stimulation and some oral but I just could not get hard.  It was horrible and I could tell she was quite disappointed and as I said I was really embarrassed.  It got really awkward between me and Althea quickly and she got dressed and left.  Usually she sleeps over whether we have sex or not, so this was quite unusual.  I had planned a long, lazy weekend in bed.

Did you have an orgasm? Did your partner(s)? As I said above, I struggled to even get hard so I didn’t, for me it was quite embarrassing.  I did give Althea one with the finger job.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, Althea and I don’t use protection. However as part of our arrangement we are monogamous with each other and I know Althea is on birth control.

What were your REASONS for having this hookup? I wanted to.

Were alcohol or drugs involved? If so, how much? I did have a glass of wine with dinner.

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? It was awkward between me and Althea for a few days, but that next Tuesday I was able to talk her into coming over again.  I in her words “fucked her brains out” and had no issues preforming and pleased Althea several times and came myself several times and things between us are now fine, but she did complain she was sore for about a week afterwards.
I like Althea and really enjoy spending time with her and the sex is great, but our relationship is more of an arrangement and not that serious.  She is due to get her degree at the end of this term, she has already had a few job offers, and I have a feeling at that point she will be looking to split up.

To whom did you talk about the hookup? How did they react? Haven’t really told anyone exactly what happened but I did talk to a few guy friends and learned that an inability to preform is quite common, it just seemed to have hit me a little later in life.

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

Do you regret this hookup? If so, why? Honesty not really, only what happened.

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? I think the best part was the thrill I got from pleasing Althea, I think the worst part was my inability to preform.  I think that was due to a combination of jet lag, stress, and wine.  Since then I have no issues in the bedroom.  I have come to the realization that I am getting older and I know it’s a little cliché but I prefer the company of intelligent, attractive, and much younger women.

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

All things considered, how NEGATIVE was this experience? Fairly negative

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