Sinking My Shaft In Sheila

by Jackrabbit Slim

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? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny 24/7
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? 2

Sinking My Shaft In Sheila

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than a month

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? Sheila was a 5’ 10” blonde married milf with 42 DD titties with minimal sag, a nice spankable ass and a nice shaved pussy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Sheila and I had met about a month earlier and had emailed each other. I began to call her office at lunch hours to continue with the groundwork. Sheila’s hubby went out of town for work and she left her two daughters with her hubby’s partners and made the hour trip to my house. She came over to my place every two or three days, where we would make out, give each other blow jobs and get naked. We would work each other up and she would rub her pissy on my cock. When she would try and push down on it, I would slightly move to the side, so it didn’t slip in. We did this for three or four sessions, as I would get her all worked up but denied Sheila the cock she so desperately wanted. We would calm down and relax, but she went home wet, horny and craving my cock.

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? Sheila and I had planned on meeting up again, as she had told her in-laws that she needed to go to the city overnight for work. Instead, she came over to my house, where I had everything waiting for her, excluding condoms. I planned on cumming inside Sheila a few times that night.

When Sheila and I jumped in the bed to warm each other up, it was like the preceding four nights together; lots of foreplay, licking, sucking, neck get and making out. Sheila was going to try and mount me again. She fully expected me to move my cock to the side, but I didn’t. I let her rub her wet pussy lips on the head of my cock. She let out a moan of surprise and she jammed her pussy down on my cock. After the days of reason for both of us, it was glorious to feel the velvet insides of Sheila’s pussy. Sheila rode me and I felt her pussy start to erupt, which caused my balls to swell and blast a load of cum into her. She ground her pussy into my body super hard and had a screaming orgasm.

Once Sheila was done, I asked her to see my handiwork. I love seeing my cum deep out of a freshly fucked pussy and she showed it to me with great pride. We basked in the afterglow and then got excited again when I asked her to get on all fours and mounted her doggy style. Sheila was practicing her Keigel exercises on my cock and it was awesome! She begged me for a second load and I gave it to her!

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? Sheila and I continued to fuck each other for about a year. We both felt great, as we were super sexually attracted to each other and couldn’t get enough of each other. I had no expectations other than I get to continue to fuck her bareback as long as possible. She was fantastic!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? Nobody. She was my married slut secret.

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? Sheila’s enthusiastic need to sexually satisfy me. I got to cum inside her

What was the WORST thing about this hookup? She was married. Not that I wanted to be with her, I just wanted to fuck the shit out of her 24/7/365.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It sure did. Got me hooked on the married women.

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

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

What do you think about the Casual Sex Project? Awesome!

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