My Reluctant Meeting With An Extra Sized, Extra Experienced Older Woman



What’s your gender? Man
How old are you? 64
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

My Reluctant Meeting With An Extra Sized, Extra Experienced Older Woman

How long ago did this hookup happen? 43 years

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

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? Hazel was huge and not that attractive, but extremely sexy, especially over the phone. She had called me at work several times and engaged in phone sex with me. I confided that I was just recently married and my wife and I both had little experience. She offered the idea that since she was very experienced, at the age of 38, she would be willing to teach me. Her voice was dripping with sex in her native southern drawl and after about the fifth call I said I might consider it. She gave me her phone number and said to call her if I was interested.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was frustrated at the lack of sex and my wife’s unwillingness to be adventurous in bed, so one Saturday when I was horny and had gotten turned down by my wife, I picked up the phone and gave Hazel a call. She said to come on over, but since we hadn’t met she wanted to warn me that she was a big woman. I told her I was a little on the larger size myself and she said she warned me that she was more than a little larger. After getting directions to her apartment, I drove there and circled the block about 8 or 9 times before I summoned up the courage to knock on her door.

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? She opened the door and ushered me in. She was right, she was huge, probably over 350 pounds and not exactly attractive, but her mannerisms and her voice were the saving grace that kept me there. She asked me if I still wanted to proceed and I confided that I was a little unsure of my self. She told me to sit on the sofa with her and just talk. She proceeded to ask me what I wanted sexually and seduced me with her southern drawl dripping with sex. Her conversation stiffened my dick until it was easy to see my erection tenting up my pants. That’s when she reached over and started stroking me through my pants. She then took my hand and led me to the bedroom. There she pulled off my clothes, all the while giving my cock an occasional stroke to keep me rock hard. Then she pulled down her shorts and underwear and laid back in bed. She guided me in and we fucked in the missionary position. While we were fucking, my head was spinning, I was excited to be fucking someone new, but also feeling guilty for what I was doing. Her pussy wasn’t exactly tight but her movements were giving me a sensation that was different from anything I had felt before. It didn’t take very long for me to shoot my load in her ample sized pussy. I stayed in for a short while then I started to go soft. Then as I went soft, she switched around and took my cock in her mouth and started to give me a blowjob. This was a new experience for me and I didn’t know what to think. I started to get hard again, but about that time the guilt really kicked in. I remember thinking what am I doing here with a stranger. I pulled away from her and she acted disappointed. She then asked if I would lick her pussy. I told her I didn’t know how to do that and she replied that she could teach me and winked at me and said it would pay off for me as my wife would love my new skill. I considered for a split-second but told her I didn’t feel comfortable with that. In the back of my mind, I was worried about being gone too long and my wife asking too many questions. We both got dressed and talked. She expressed the hope that we would get together again and maybe even go dancing or a dinner date. The thought of that scared me. I was afraid she was wanting more out of this than what my expectations had been.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? I felt guilty and worried somehow that my wife would find out. I was also worried since she had my work number that she would pursue more of a relationship. As time has gone by, I felt a little better about it. I did learn how to talk frankly about sex, something I hadn’t done before. It did plant the seed for how good a blowjob could feel and that women do like oral as well and eventually I persuaded my wife to try both.

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, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more desirable, Revenge / Getting even, It was easy / convenient

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

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Prescription sedatives (Valium, Xanax, Diazepam, Quaaludes, Phenobarbital)

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

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? A little bit

Why do you regret this hookup? It’s the only time I have been unfaithful. My wife is the only other partner I have had.

What was the BEST thing about this hookup? The experience in actually having an open conversation with a woman about sex and what I liked. The ego boost of having a woman want me sexually.

What was the WORST thing about this hookup? Some guilt.

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

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

Anything else you want to add about this hookup? I learned good sex doesn’t have to involve a perfect body. Sexy attitude and sexy conversation can be better than a perfect body.

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? Although this was a one time experience, there have been a couple of other times where I have tried to search out to see if I could find a similar experience. This has been when my wife has not been sexually responsive. I fantasize about an older or more expert woman to this day.

What do you think about the Casual Sex Project? Interesting, I like to read the variety of experiences.

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