Servicing My Boss

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? horny all the time
How many sexual partners have you had in your life (including oral sex)? about 55
How many hookup stories have you here posted before? several

Servicing My Boss

How long ago did this hookup happen? three weeks 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 more than 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? My boss, Ella, is 9 years younger than me. She is about 5 foot 6, and 150 pounds with black hair, large boobs, a nice ass, and she always shows some nice cleavage when she dresses for work. She is of Armenian background and is currently single. When I am in her office, I can’t help but look at her cleavage. I try not to, I honestly do, but my eyes are drawn to her boobs. I know she sees me looking. I have fantasized about sucking on her tits for years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in Ella’s office talking with her about a project, and of course, I was looking at her boobs. I know she saw me looking and I tried to avert my eyes, but I just couldn’t help it. It was nearly quitting time and she asked if I wanted to join her for dinner to talk about the project some more. I agreed. We met at a local diner and talked some more but of course, I kept looking at her delicious boobs. She had never confronted me about my looking but now she asked: “do you enjoy looking at my boobs?” I told her that I was sorry, but I did enjoy looking because they look so nice. What she said next really surprised me: “would you like to go back to my place and get to know the girls better?” I told her I really would. We got up and left for her place.

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 got to her place and got in the door. She closed the door and turned around and pressed her body up against me and we started making out. I unbuttoned her top and freed her boobs, bending over to suck on her nipples. She had nice, hard, big, pink nipples and as I sucked one and then the other into my mouth, she would moan. She reached down and rubbed my cock which was rock hard already. She unzipped my pants and reached in as I was sucking on her nipples.

She took my cock in her hand and led me to her bedroom. She turned and dropped to her knees and took me in her mouth. It was wonderful, her hot mouth sucking me into her throat, her tongue running over my head, her hand massaging my balls. She first took one nut into her mouth and sucked on it before taking the other one and sucking it. She was sucking me so wonderfully and I was getting close. She must have known it because she really started going at it until I nutted in her throat. I did warn her, but she just sucked harder. She made sure she got all my cum and then pushed me back on the bed. She helped me out of my clothes and started taking the rest of hers off. Her breasts were magnificent, probably a 38 DD. I started attacking her boobs again and ran my hand down to her bald pussy. I fingered her pussy and ran my fingers over her clit for a while until I knew she was about to cum and started seriously finger fucking her. She came all over my hand. It was a soppy mess, but I loved it. I went down between her thighs and began eating her sweet pussy as she was still cumming on my fingers. She tried to push my head away, but I wouldnt let her. I sucked her clit and her big pussy lips and she was moaning like a banshee. After she had cum a couple of times, I took my once again hard cock and ran it between her huge tits. I just had to fuck her tits at least once. I ran my cock in and out with her taking my head between her lips each time I pushed through. I then laid down on my back and told her to straddle me. She did. She sat down on my cock with her wet pussy. She was nice and tight. She later told me that her ex was much smaller than my 7 1/2 thick inches and she loved the way I filled her up.

She rode me cowgirl for about 5 minutes and then asked that I take over. I rollled her to doggie and pushed in deep. I worked in and out of her enjoying her pussy for another 5 minutes or so. By this time, I really wanted to load her pussy up and asked if I could cum in her. She said she was on the pill and to cum in her pussy. I rolled her onto her back without pulling out and proceeded to long stroke her, picking up speed until I was pounding away at her sweet pussy. She was moaning and finally, I felt her pussy clamp down on my cock as she had a massive orgasm. I was close but not quite there yet and continued to pound away. After another 2 or 3 minutes, I felt my balls tighten and I shot rope after rope of thick sperm into her. After I finished filling her up, I laid on her until my cock shrank up and she pushed me out. We laid in bed cuddling as she felt my limp cock with her hand and began stroking it, reaching down, playing with my balls and finally going down and cleaning me with her mouuth. After a while of her doing this, she got me hard again and she climbed on for another round. We fucked for about 2 1/2 hours before I told her I had to get home.

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? The next day we didn’t talk about it, but I did text her toward the end of the day and thanked her for a wonderful time. I also asked if she thought whether or not we could have a repeat performance. She said that she thought we should soon. We met up the following day and had another 3 hour fuck fest and 4 more times since then. I think I have found another FWB.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Power / Dominance, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? just her, no one else

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? A new FWB, great sex, and I finally got to suck and fuck the tits that I had been fantasizing about for several years.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? feel bad about cheating on my wife, but our sex life is not up to par and I need some relief.

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