MILF Creampie

by AJ

What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Asia
What country and/or city do you live in? Malaysia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Classified
What’s your current relationship status? Single
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? N
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? None

MILF Creampie

How long ago did this hookup happen? 2017

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Paid sex

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? She’s a Filipino staying in Malaysia. Had a slightly chubby body, natural big boobs, and definitely a mature woman look. I got to know her through a Craigslist ad, and I thought it was a good chance to try out someone older than me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I decided to call her last year, and we discussed her rates and such. Pretty reasonable, had no complaints. When I asked her about having sex without a condom, I was surprised that she said yes. I asked if she had bareback with anyone before, and she said it only happened with one other 19-year-old guy. Not sure how true it was, but I decided to take it anyway. I mean, you don’t get to see MILFs who let you cum inside them a lot. Initially, she charged extra for a creampie, but I managed to get a discount after promising her that I’d give her a massage and eat her out.

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 reached her place and she gave me her room number. Was pretty excited, to say the least, and all the way, my heart was pounding in anticipation. On hindsight, I should have brought my bottle of water cos it was making me really thirsty. Anyway, when she opened the door and greeted me, I felt my heart leap. Sure, she wasn’t young and beautiful, but I’m not picky. Plus, a mature woman has a quality of beauty of her own. I took a quick shower while she waited in bed for me. I paid her, then we got down to it.

The first thing I did was to massage her. I’ve never massaged anyone before, but I think she liked it. I was body sliding on her back while massaging her boobs when my penis accidentally went inside her, and she made a soft moan. Well, since it was in there, I started pumping away. After a while, I pulled out and ate her out as promised. She told me she loved it when my tongue dug around inside her. Then, I told her to ride me, which she happily obliged. For me, there is something really arousing in having a mature woman ride you like they were in control.

Needless to say, I enjoyed it so much that it didn’t take me long before I came inside her. Oh, how I loved the feeling of her warm insides squeezing on me as my penis throbbed and spurt out cum. She told me she felt it inside her. When she pulled out, she decided to keep my cum in her, which I’m totally okay with. She was already past the fertile age anyway, so I’m not exactly worried about getting her pregnant.

How sexually satisfying was this hookup? Very

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? We stayed in bed and chatted a bit for a while before I left. Didn’t feel anything about it, but I thoroughly enjoyed it. Might want to visit her again someday when I have the time.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Fertility awareness (days counting, temperature)

What were your motives for this hookup? Fun, pleasure, horniness

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? A little bit

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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.

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? I get to lay with a mature lady AND cum inside her at the same time. What’s not to love?

What was the WORST thing about this hookup? Possibility of health concerns. Will do a checkup to ensure I’m okay.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

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? She’s a really nice lady, and funnily enough, we still maintain contact. She doesn’t fuck for free, but we get along in chat pretty well.

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? No comment.

What do you think about the Casual Sex Project? A pretty good place to read raunchy stuff and motivations behind sex.

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