What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Me tucky
Highest education received: High school diploma
What’s your occupation? NA
What’s your current relationship status? Engaged/Married (open)
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? Exhibitionist
How many sexual partners have you had in your life (including oral sex)? 80+
How many hookup stories have you here posted before? 3

Word of Mouth

How long ago did this hookup happen? Recently

What was your relationship status at the time? Engaged/Married (open)

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

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? Glenda was an attractive 58 year-old. Small chested, nice ass,skinny,could use some more meat..was beginning to show signs of aging,but you would not think she was 58. We used to work together in the same restaraunt she still works at and she was actually a family friend for 20 years previous. When I worked there,I always thought she was way to intense and stressed. She was a Christian woman,although I don’t think her and her husband went to church often. She is definately not someone I ever thought would be up for a good fucking just for fun. But I started noticing the signs during my once a month visits to the store.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When I am hard I measure 10 1/4×2 1/4x 1 1/2 inches with a 2 5/8 inch head. Yes,I have been measured several times by curious women. I used to mess with a few girls at the place when I worked there and one girl told me that Glenda had “jokingly” asked about sex with me and informed me that she had told Glenda all about me. Planning actually was involved on my end because for some time now I had tried to find a reason to visit Glenda in the store before open actually occurred. I am quite sure Glenda felt she finally had her opportunity to quench her curiosity that had built for 6 years! Every time I would go in while it was open she would hug me and get a good glance at my crotch and then inadvertently brush a body part against my crotch.

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 went to the store about an hour before anyone else would be there. Being that we knew each other she unlocked the door and locked it behind me. She gave me my customary hug and I hugged her trying to feel everything I hand in the small of her back and one partially on the side of her hip with my fingers on her ass. I WAS getting turned on!!She looked up at me with a naughty grin as she put her leg up against my cock. We broke it off but we were both nervous and giddy. She took a seat in the dining room and I stood beside her as we smoked. Every time she would look at me her eyes would end up looking at my cock which was half hard right now. I raised the stakes a little to see how she would react. I put my hand in my pocket and started non-chalantly rubbing myself. It worked,she wouldnt take her eyes off of it! So naturally I was getting harder and harder! Suddenly she got up and looked out the windows leaning over a table and bench. I came up behind her and wrapped my hands around her tits and started grinding that sweet looking ass! I had her shirt partially unbuttoned and pushed her bra up, as I grabbed and caressed her bare droopy tits she let out a moan! In the same instant I unbuckled my belt and pulled my pants down. I was so hard my cock was sticking straight out! She turned her head grabbed my cock,let out a OMG,asked me what I was doing and said she thought this was a bad idea and she couldn’t do it!! I turned my attention back to getting her shirt off,and when I did ,she was still slightly bent over, for some reason the degree that those little tits were drooping turned me on to a whole other level! I told her at that point I was going to fuck the hell out of her. I started working on her jeans next,I got them down to her knees and then started kissing her back as I slowly pulled her panties down exposing a slightly droopy but oh so sweet 58 year-old ass!! I started kissing her ass and telling her how sweet it was as she started letting out some grunts and moans. I stood back upright and she started ,almost hysterically, telling me it had been over a year since the last time she had had sex. She grabbed my cock and started stroking it,telling me that IF I did get it in her ,her husband would know she had been fucked. She was a little woman,I would say she weighed 95 lbs at the most. I backed up and she turned around and I finally got to see her little bush that was almost half full of gray hair and that’s when she started telling me she had only been with one man for 35 years. I started sucking those little tits and and fingering her pussy..I could feel all the inhibition she had left was leaving! That’s when she told me about knowing I had a big cock and that she sisnt want to fuck once again telling me she didn’t want her husband to find out. She sat down on the edge of the bench,with her jeans still around her calves and I started jacking off making contact with her lips and face rubbing the pre-cum off on her lips. She took over and I went back to work on her tits and pussy with each hand. She was so wet she was dripping! I started talking dirty to her and finally slipped my cock in her mouth and gave her a few pumps. She was turning me on so much by then I was about to blow, between moans she then told me to fuck her!!I picked her up laid her on her back and started trying to get in her tight,wet pussy! It felt like a virgin. I was only in half-way and she was screaming her head off. I was going slow and I started to get deeper and speed up. She was so tight she was bleeding a little,as I was about to cum I started throwing it to her hard. She was enjoying it more and more as she had her knees pulled up as far as she could get them! She was cumming so much my cock was covered in a thick layer of white and it was running down her ass. Then,I started to pump my load in her. I cummed so much ,before I got done it was running out!

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? Nothing for me has changed toward this person,other than knowing how cute and sexy her body is for a 58 year old,I would like to fuck her again. We will remain friends like we were before it happened.

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), 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? 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? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I got to fulfill a fantasy of my own. I had often imagined fucking her as I was jacking off.

What was the WORST thing about this hookup? None on my end. I think she felt guilty.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No it hasn’t changed my opinion. Women can say what they want,but it has been my experience that they are curious about the size of a cock from time to time and sometimes develop a desire that they can’t stop. I have had numerous hookups simply because of word of mouth.

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? This hookup happened purely from something she had been told about and her desire to see if it was actually true. It was my pleasure to show her.

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 love NSA and experiencing sexual pleasure with others. I love to see and feel women’s naked bodies!

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

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