What’s your gender? Woman
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States Wasatch Front
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? CPA Accountant and Controller CFO
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Reserved at first, pursuing when ready
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1
The President And The Controller
How long ago did this hookup happen? Monday, July 31st
What was your relationship status at the time? Engaged/Married (monogamous)
How would you best classify this hookup? Fuck-buddies / Booty call
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? Jack is 36, single, never married. 6′ 2″ tall, firm body and blonde hair with blue eyes. He is my boss and President of the company I work for. I have worked at the CFO/Controller position for almost 3 years now. Jack and I have always had a very professional relationship and it stayed there until recently. About 2 weeks ago I caught Jack staring at me from his office across from mine. I smiled and he was like lost in space, then caught my smile and smiled back. Later that week I caught him watching me walk down the hall, checking out my 49-year-old ass. I am not gorgeous, rather plain, with green eyes, black hair, a curvy body from having 2 kids. I am not fat, but I am not skinny. The next day Jack brushed by me several times, his hand brushing my hand, winked at me and walked on. For the first time, I had it confirmed that my boss was interested in me.
This week he came into my office, shut the door and we received some changes he is going to make to the company in terms of responsibilities of managers and we were going to let several people go so I needed to have their payroll done. I phoned my payroll person/controller and they would have the check ready at the end of the day on Friday.
Jack then invited me to lunch and being hungry and having forgotten my lunch I thought sure, good time perhaps to see what his intentions are. I wasn’t in love with Jack, but I was attracted to him and had thought what it would be like to have a sexual liaison with him.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am married, have been for 30 years, and I have cheated once on my husband with a fellow co-worker. That affair lasted 3 to 4 years and was incredible, sexually. My husband is a wonderful husband, loving, helpful, and earns a great income. However, I lost interest in him sexually at the start of my first affair when he no longer turned me on and gave me multiple orgasms during sex. I didn’t and wouldn’t leave him, but when a good opportunity presented itself, well, I had to taste the food to see if I liked it.
Jack drove me to lunch which was a very good lunch and afterward, as we got back into his car, he started to run the a/c and then he reached for my hands with his. Taking my hands in his, he moved across and kissed me. At first, it was an exploratory kiss. A simple peck to gauge my reaction. I liked it so I kissed him back in the same way as his hands interlocked with mine. This time he kissed me again and opened my mouth to let his tongue enter into my mouth. We began to make out, my tongue in his mouth, tasting his mouth and his in mine. I felt his hands guide mine to his crotch, and I began to rub what I felt which was his right testicle. His hands went up to my breasts and for the last 2 weeks, I had begun to wear a low cut blouse that showed my cleavage. Jack now rubbed my cleavage and said: “Oh I want those wonderful sisters.” I was getting turned on, really turned on, so I replied instantly with “Let’s go somewhere and I’ll let you enjoy them.”
Instantly Jack stopped petting and making out with me, we buckled and drove down the street. We checked into a Marriott, under Jack’s name and with our key in hand, went up to the 4th floor. In the elevator I kissed him with passion a few times, until the door open and taking my hand, Jack led me down the hall. At the door, he unlocked it and inside we went.
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? Once the door was shut we instantly started making out again, and I removed his shirt and t-shirt to reveal a firm upper torso. I ran my hands over his chest and then held his head in my hands as I kissed him over and over again. Jack now removed my blouse, my bra and instantly his hands were on my large and exposed breasts. He rubbed them as he kissed me, and then kissed down my neck and took about 1/2 of my right breast into his mouth. He sucked on that breast, rubbing my left one and it felt so damn good again. I knew then we were going to fuck each other.
I moved Jack to the bedroom slowly, and there we laid on the bed where for twenty-five minutes he sucked both of my breasts, alternating between them. He sucked my nipples, making them hard and as he enjoyed himself, moaning at times. I undid his belt, then the button on his pants, then his zipper and I removed his pants, boxers, and socks. Jack was now naked and his dick was hard, erect and ready for action.
Jack kept sucking my tits and nipples, arousing me as I began to stroke his dick and also use my fingernails on his testicles, slightly touching them with the fingernails. I felt Jack now undo my pants, removed them and my panties, and my socks and now I was naked. I was aching for Jack, my pussy was hungry and I wanted his dick in me. I began to kiss him and moved him on top of me as I spread my legs and wrapped them around him. Jack looked at me as my left hand grabbed his dick and I used his head to rub my vaginal opening, turning me on more.
I was soon soaked, so soaked that I began to soak the sheet. I now kissed Jack intently and while looking into his blue eyes, and using my left hand still, I drove his hard dick inside of my vagina. I felt each inch as it moved inside of me, and though not as big as my first lover nor my husband, Jack had girth. I could feel his dick completely fill my vagina and push it out. I got butterflies in my stomach as I now held Jack close, his chest on mine as he slowly began to pump his dick in and out of me.
We kissed as Jack fucked me, made love to me, as he sped up and slowed down his pace to make it last longer. Several times he got me so close to having multiple orgasms just to back out or slow down. I could feel my vagina swelling and begging for Jack to keep up the pressure on my spot. He hit my spot perfect. Again Jack began to shove in and out and this time I got so turned on that I drove him out, flipped him on his back, mounted him, and then fucked him so fast I am sure I was nothing but a blur.
I felt that wonderful warmth begin in my vagina and chest, swell up into my neck and face and explode from my vagina as Jack’s hard dick did its job and stimulated my g-spot. I screamed in pure pleasure “YES” and “More” and “GO FASTER!” I suddenly felt his penis harden more, grow thicker as it swelled with his cum and then I felt that wonderful stream of warmth as he ejaculated multiple times into my vagina.
I looked at the alarm clock as we I fell on Jack’s chest. We had been making love and fucking for over 50 minutes! I kissed Jack, and we talked about this. I explained about my husband, that I wouldn’t leave him but I would agree to be Jack’s sex partner and lover as long as we were committed to each other in that way. Jack agreed and then we started to do foreplay again, teasing, laughing, talking and then kissing, touching, sucking, fucking again. Two more times we did it as I called my husband and said I had a late night working and going over stuff with Jack. I forgot what it was like to fuck a man who could really fuck you and wanted to fuck you and just be with you.
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? Jack and I fucked on Monday, the 31st, made love twice on the afternoon of August 1st and made love today, all day, while going over company financial records. We plan to keep fucking as much as we can though we know we have to control it, perhaps 3x a week so we actually do run the company.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel more desirable, Boredom, It was easy / convenient
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? Somewhat
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.
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? Not at all
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Connecting to a man who fulfilled my sexual needs and physical needs. The sex was excellent.
What was the WORST thing about this hookup? Getting caught up in making up for no sex for either of us for 2 years.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. Keeps my marriage going and relieves my husband from having to pretend to meet my needs sexually when he doesn’t. Does in the other areas though.
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? Size matters a little bit, but girth is what I love the most. I like a thick dick and fills me up, and pushes my vagina wall out. Turns me on!
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? We all want it, period. We should give in more to it, have short affairs if married or not, and relax about it. Casual sex is good for the heart.
What do you think about the Casual Sex Project? Good stuff.
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