Unexpected Hookup With a Former Client

by M

Gender: Male
Age: 30
Race/ethnicity: White
Current location: Oregon
Highest education received: College degree (eg., BA, BS)
Occupation: Bookkeeper
Relationship status: Seeing Someone
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)? 13
How many hookup stories have you here posted before? Three

Unexpected Hookup With a Former Client

How long ago did this hookup happen? Last Night

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? B is a somewhat pretty brunette, not overly attractive.  She is in her late thirties, 37 or 38 (age difference was not an issue, current girlfriend is around the same age and the one before her was in her forties).  She is about five six or five seven, a little shorter than I am.  I didn’t know it since she always dressed very conservative but she was actually quite fit with nice D cup breasts. She owned her own business, but was generally pretty quiet and soft spoken. She hired me to do some bookkeeping work for her business last summer and she was only a client for a few months.   She was also married.  I got the impression she didn’t like me very much.  I had never given B a second look and honestly, she was not someone even remotely on my radar as a potential sex partner.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? B called me a few days ago needing some paperwork for her taxes.  I am on the road a lot for work and was passing through her down yesterday and I offered to put it together and drop it buy her office.  I feel I should also share I have a girlfriend right now.  She is also on the road for work most of the time but there are not too many places to travel to for work around here so every week or two we are usually in the same town or close so we meet up.  I had actually checked into a hotel early yesterday and she and I had enjoyed a few hours in bed before she got back on the road.  Having just had sex, I wasn’t even remotely horny.
In the early evening I went to meet B, dropping the paperwork by.  Afterwards she asked if I wanted to go for dinner and I figured why not.  We went to a brewery and ordered dinner.  B started coming on to me here, her leg rubbing against mine a few times but I wasn’t really paying attention.  Finally she went to the bathroom, and came back with her hair down and a few buttons open on her blouse.
Women don’t usually come onto me like this so I had been missing the signs.  B sat down next to me in the booth, and put her hand on my thigh and then on my cock and goosed me for a minute.  When I asked what she was doing, she took my hand and stuck it down her pants so right on her pussy and asked if I liked what I felt and if I said yes.  At this point B asked if we could go to my hotel room and I agreed.

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? I was a bit nervous, it had been a long time since I had a new partner (current girlfriend was someone I had been with before).  However it was as if a switch had flipped inside B, she was coming onto me the entire way and grabbed at me the entire walk over, fortunately I was staying across the street.  We made out a bit as soon as the door closed to my room, I had my hands on her waist but anytime I made a move for her chest or ass she moved them back.  I learned pretty quickly she liked to be in control.
She told me to undress and sit on the bed.  B did a dance as she took off her clothes and she climbed on top of me and we made out naked for a bit.  Here i learned how strong she was and how fit, and how nice and big her breasts were.  Again anytime I moved my hands towards her ass or chest B would move them away.  Finally after a few minutes she let me and I grabbed her ass a bit and finally get my hands on her breasts.  I played with her nipples before finally bringing my mouth to them she moaned a bit before finally grabbing my cock and placing it inside her and mounting me.  She rode me for a while until I came, and she was quite loud and screamed a bit and I think she had an orgasm.
Afterwards she climbed off me and asked if she came for a while and I then went in  the bathroom, I think she was a bit embarrassed.  I went into the other room to get some work done.  About an hour or so later B came in and asked me to take my pants off.  She sucked my cock, and was quite good at oral.  I decided to just sit back and enjoy the blow job.  It took about fifteen minutes and I exploded in her mouth and she swallowed. She told me to come join her in the bedroom when I was ready.
I finished my work up and I went into the bedroom.  B was laying on the bed naked, and I undressed again and climbed on her.  We made out a bit and I penetrated her and rode her in missionary until I came again.  She was loud again and moaned a lot.  We were both tired after this and fell asleep.
When I awoke in the morning B was asleep next to me.  I went to take a shower and B joined me and we made out and grabbed at each other.  We ended up fucking in the hall there between the bathroom and bedroom and B mounted me as I leaned against the wall.  I sucked on her breasts again and again came.  I was pretty sore at this point and B put her clothes on.  I went and got breakfast downstairs and we talked a bit, we hadn’t much last night.  I learned she wasn’t very happy at home and a little more about her.  I mentioned I thought she didn’t like me and she laughed and said she didn’t very much but maybe that was what had made the sex so good.  We agreed this never should happen again and B left and I packed my car and drove a few hours to my next job.  I did really enjoy myself and letting go a bit and B was a great lover.

Did you have an orgasm? Did your partner(s)? I did four times and B did several times as well.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Honestly, we did not discuss STIs at all and I finished inside B several times.  However B visibly took a morning after pill in front of me and told me she was being very careful because she did not want to get pregnant by her husband.

What were your REASONS for having this hookup? Still trying to figure out what my reasons were, but I think the biggest one was because I have never had a woman just come onto me like that.

Were alcohol or drugs involved? If so, how much? We had a cocktail each, not much

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? As I said B and I decided this should never happen again and she is not a client and since I dropped the paperwork by for taxes this year I have no reason to see her again.  I do however pass through her town quite often but I am not planning on looking her up.  I have a girlfriend who I am developing feelings towards and can see a future with.

To whom did you talk about the hookup? How did they react? Haven’t told anyone and I am debating about whether to tell my girlfriend or not

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

Do you regret this hookup? If so, why? A bit actually.  First because I knew B was married and even though we are not exclusive, I feel like I cheated on my girlfriend a little.

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 part was the sex, it was great.  Worst part was is the guilt I feel now about the whole night.  I hadn’t been with anyone else the past few months since I started seeing my girlfriend again.  This has made me realize maybe she and I should have the exclusivity talk, I would like to pursue a future with her.  This hookup hasn’t changed how I feel about sex at all, but I do feel like B’s marriage is about over.  I also get the feeling like I am not the first guy she has done this with.

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

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

Anything else you want to add about this hookup or anything else? Just wanted to add that I wanted to share this while it was fresh in my mind

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