Servicing An Account Rep

by Director

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
What country and/or city do you live in? USA
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? 5

Servicing An Account Rep

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. We had hooked up a few weeks before at a work event and bout of us were eager to fuck each other again

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? E was a Account manager and would travel visiting different account offices. She had said that she had an account that need some “Executive attention” and I needed to visit the offices with her. She had planned the entire week. When I asked her why we needed an entire week for a single account she just smiled and said the account was very demanding and needed lots of attention. I arrived at the hotel about 3 hours before E. I headed up to my room and started working on the laptop. When E arrived she dropped her stuff off at her room then came down to my room. She was wearing a nice form fitting one piece dress that showed off her ass and breasts quite nicely. And I started to get hard instantly I was working at the desk. She sat in the chair and began working on her laptop.

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? We both worked for about 30 min when I heard her close her laptop and walk up behind me. She wrapped her hands around me and started nibbling on my ear while she massaged my cock through my pants. Once she had me nice and hard she bit my ear and said “Time to service the account”. We started kissing and she began to undress me as we made our way to the bed. We got to the foot of the bed then she dropped to her knees and started sucking on my cock. E knew how to service a cock and seemed to really enjoy it. When I was close I told her I was about to cum but she just looked up at me and sucked harder. After I unloaded in her mouth she stood up and smiled saying “You don’t need to tell me when you are about to cum, it spoils the surprise”.

She then took her dress off and pushed me down on the bed. She was shaved smooth and crawled on top of me sliding her pussy up my body and pausing to grind against my cock while we kissed. I started to position myself to slide inside her but she moved forward continuing up until she was straddling my face. She lowered her pussy down onto me and I started to lick and suck on her while she leaned against the headboard. After a few min she laid on her back and pulled me over to finish eating her out. Clearly it was my turn to do some account servicing. As she got close to orgasm she started to push my head away like before but I held firm continuing to suck on her. Then all of a sudden she wraps her one leg around my back and pulls me head in as she starts to quiver from her orgasm.

Once she relaxes and recovers a bit we start to spoon naked on the bed. We cuddle like this for about 15 min before she starts grinding her ass against my cock and getting me hard again. As I firm up she rolls over and says “You need to fuck me,” then rolls me onto my back and straddles my cock while we kiss. She reaches down and guides my cock into her moist pussy letting out a soft moan as I enter her. It’s a nice firm fit and takes a few thrusts before I’m all the way in but it felt so good. I mentioned how tight she was and she responds with this big smile saying, “You’re much bigger then my husband”.

She rides me like this for several minutes then climbs off and turns around with her ass facing me. She tosses her hair to the side and looks back at me, smiles and says, “Fuck me hard”

I slide into her from behind and grab a hand full of hair pulling her head back and grabbing her waist with my other hand. As I start to pound away she begins to moan. I ask if this is what she wants and E says, “Oh yes”. I pound her hard and her moans continue to grow until she collapses down onto the bed. I keep fucking her and she says “Harder”, “Yes harder”, “Yes,” as she begins to shake as her orgasm washes over her.

I laid down next to her and start to rub and massage her back while we recover. She rolls over and begins to stroke my cock and says “You didn’t cum, Do you think we can get this big guy to cum for me once more”. At which point she slides down and begins to suck on me.
Now I am spent. I have been married for 9 years at this point and sex for me never lasts more then 15 min anymore. But her mouth and tongue felt amazing. She sucked and massaged me for several minutes then climbed on and started riding. She got her workout and I loved every minute watching her tits bounce. She was starting to get close to orgasm again and asked how close I was. I explained I rarely cum from cowgirl but she was welcome to keep riding me. She smiled and kept going but was getting tired. So finally I flipped her on her back pushed her legs up and started pounding missionary. I started to pick up the pace and she asked if I was close. I said yes and where did she want me to cum. She wrapped her legs around my back and said “Don’t even think about pulling out”. She started massaging her clit with her hand while I kept pounding. I felt the pressure build inside me and then I began to unload. She closed her legs tight around me holding me in as her 3rd orgasm began.

We got up and showered together and got ready to go get some food.

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? We went to dinner and started to talk about what the week looked like work wise. What I thought was going to be 2 days full of visiting accounts around the city was really a couple of short visits to local accounts in the morning then afternoons and evenings free for us to go see do and fuck wherever and as much as we wanted.

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, Attraction to partner(s), Emotional intimacy, closeness, connection, Power / Dominance

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

Did you consent to this hookup at the time? I gave enthusiastic consent

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… this became a file loan affair between 2 married people. We were very successful in keeping it quiet,m.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? This woman was amazing and had a sexual appetite like I have never seen

What was the WORST thing about this hookup? The week had to end

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I did not realized how much I liked sex until I met E

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

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