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What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Singapore
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 3

Anal Creampie My Other Sister In Law

How long ago did this hookup happen? 1 August 2019

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

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

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 elder sister in law, J, lives in the UK. During the summer break, she returned to Malaysia with her daughter for the holidays. She is slim and fit, 35 y/o, has long brunette hair, B cup breasts, and a tight ass.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months back, my other sister in law, F whom I fucked during Chinese New Year, (a story that I’ve posted before) told me that she confided in her elder sister J about the sex we had together. I was shocked and afraid that my wife would find out from J, but F assured me J would keep it a secret. I asked F about her reason for telling J and how she could be sure it would remain a secret. F told me that she was 100% sure because their conversation ended with J asking F if I was ok to have sex with her as well. Hearing that, I was caught off guard and just simply said OK.

Fast forward to the 1st of August, my wife and I returned to Malaysia from Singapore for a short holiday so that my wife could see her niece (J’s daughter). I bumped into J at my mother in law’s house. She whispered to me, asking if I had heard from F about the proposal to have sex with her. I asked her why and if she was ok with the idea of fucking her younger sister’s husband. She told me she was extremely horny about the taboo of it and the details from F about our sexual encounter and wanted to have one as well. I got a hard on just hearing her sort of begging for me to fuck her and asked her when she wanted to do it so we could plan something to get away from her daughter and my wife. She told me she had booked a hotel room for the evening, and she told the others she had made dinner plans with her friends as an excuse. After that, I told my wife that I had to leave during the evening to go back and visit my parents and my wife said OK and not to worry about her. Once I got the OK from my wife to leave, my mind started wandering around, thinking about how I was going to fuck J whom I have secretly had a desire to pound since I first got to know her.

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 got to the hotel room and J opened the door wearing a bath robe and sheer stockings on her legs. She took my hand, closed the door, and led me to the king bed where she asked me to sit on the edge. She removed her bath robe revealing her sheer black bra, matching thongs, garter belt and stockings. I was so turned on. I held her waist, pulled her over to sit on my lap and started to french kiss her. You could tell she was craving it pretty badly by the way she removed my shirt furiously and unbuckled my pants quickly. She put her hands in and pulling my stiff cock out from my boxers. She then started stroking my cock and playing with the tip, as we were still french kissing. Having her hands going up and down my cock, I pulled out from our kiss, unclipped her bra and started licking and nibbling on her hard nipples. She arched back and let out a soft moan as her strokes got faster and faster. After tongue playing her nipples for awhile, she pushed me down with my back on the bed, climbed up to my face, pulled her thongs to the side and started grinding on my face. She was cleaned shaven as i thought she would. I pulled her pussy lips apart revealing her clitoris and used my tongue to get to work. I kept sucking and nibling on her clit. Her moans got louder and she started grinding faster. Whilst all this was happening, she was arching back with her hands, still stroking my cock. She kept edging me and did not want me to cum. After a few minutes, she stopped grinding, grabbed my hair and face planted her pussy deep into my mouth, as she let out a loud moan and orgasmed on my face. We stayed like that for a few minutes until she calmed down a bit.

I got out from under her and flipped her over on her back. I removed her thong and lapped up all her sweet pussy juices. I put two fingers into her, rubbed her G-spot, and then guided my cock into her, missionary style. Her pussy was so tight that I couldn’t get all of my cock inside her initially. After a few thrusts however, I got it all in and it was so hot having her tight pussy envelope my cock. I fucked her slowly, then quickly. I started to pinch on her nipples whilst fucking her, and her groans got louder and louder. Feeling excited, she started rubbing her clit and in no time she convulsed and had a second orgasm. I too was on the verge of cumming, but decided to hold badk as I had been edged by her earlier and wanted to keep it going longer to give her a massive cumshot in the end. I pulled out of her, turned her over, and resumed fucking her in dodgy style. Whilst fucking her, I put my thumb in her asshole and she was turned on more. I thumbed fucked her asshole as I was pounding her pussy. Through her groans and moans, she told me to stick my cock in her ass. I thought I misheard her and continued fucking her pussy, but then she said it again, and this time, I heard it clearly. I took my cock out and positioned in at her asshole. I spat on her ass, thumb fucked it awhile, and then guided my cock in. It was my first time anal fucking someone. I had not done it with my wife or with F. It was very hard to get it in. She reached back and spread her butt cheeks and I slowly got the tip of my cock in. She let out a very soft moan. I slowly started rocking back and forth, putting more of my cock in her with each thrust until I got in all in. I was experiencing a different sensation and it was tighter and warmer than pussy fucking. I was so turned on and started fucking her hard. Her moans and groans only heightened the pleasure. All the edging earlier was building my cum up and within minutes, I was ready to let it all out. She told me to unload it all into her ass, and after a few more thrusts, I did just that. I shot several massive loads of cum into her ass until my cock softened up. I pulled my cock out and she collapsed on the bed. I cupped her breasts from behind and fondled them as I hugged her and kissed her shoulder and neck as she pushed out the cum from her ass. We stayed like that for a few minutes until she turned over and I gave her nipples and then her lips a soft kiss. We both headed for the shower together and cleaned each other off. After our shower, we got changed and got ready to leave. Before leaving the room, J said thanked me for the experience and said that we should do it again someday. I gave her a kiss, said ok, and with that we both left the hotel for home.

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? For the rest of the holiday, we both pretended like nothing happened so as not to arouse suspicion from my wife. Now, whenever I look at J, I get reminded of our sexual activity and get so turned on. I think she might feel the same way as well.

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

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? I told F about it as she was the one who initiated it. She asked me about it, and I shared with her the details. She got so horny that she told me she masturbated to it that night.

How would you best summarize people’s reactions about this hookup? Relatively positive

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

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

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

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