My Second Ever Lover (Cheating)

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by Madonna

What’s your gender? Woman
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Stay at home mum
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
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 Second Ever Lover (Cheating)

How long ago did this hookup happen? One month

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? We married straight after I graduated nursing at 22. We had been together since high school and my husband is the only man I had ever kissed. We have 2 school aged sons and as a stay at home mum, I have time to take care of myself whilst keeping the family fed and happy. Our sex life is a bit vanilla, 2 or 3 times a week, missionary but very loving and lacking.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Some of the school mums had arranged a ladies day at the horse races. They said it was great fun and an opportunity to glamour up and let our hair down. Six mums turned up at the track and we looked great and I felt great. I had no idea what this scene was like, there were handsome, suited up men and glamorous ladies everywhere. A group of men around our age started to flirt and buy us drinks, which seemed harmless at first, but one tall dark and dashingly handsome one became very attentive, which to me was a little embarrassing, yet exciting. He wore a wedding ring as did I, but we enjoyed each other’s company. He made sure my drink was always fresh, and I felt like I was the only person he could see. As the day drew to a close it was time for everyone to leave, and most of my group had left. It was always my intention to take a cab home but my new friend offered me a lift home, which I figured was a little naughty, and yet probably harmless as we were both married. The drive home is about 20 minutes and 10 minutes in, he said, “I see you as a beautiful woman, in a mundane existence. You don’t understand how sexy you are, and nor does your husband. I was stunned by you. Your gorgeous body needs proper attention, you need fucking and you need it now.” I was instantly wet like I hadn’t been in years, and yet I was scared. He said, please allow me to liberate you. He knew me better than I knew myself because after a few seconds of thinking about my mundane sex life, I said ok. Within a few minutes, he pulled his car into a motel and in no time he had a room key.

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 was very nervous as we went inside the room, at which point I told him I was nervous because, even though I had been having sex for twenty years, I had only ever been with my husband, and really had zero experience. He said, well this is an opportunity for you to do something for you, not for your husband, not for your kids, just for your own pleasure and satisfaction. With that he cupped my face and kissed me deep yet gentle, I had never been kissed like that, my panties were now very wet, he laid me on the bed and we kissed for what seemed like hours, then he removed my dress, and there I lay in just my panties. He started to kiss my feet and within seconds he spread my legs, he pulled my panties to the side and with one lick from my vaj to my clit, I began to convulse in orgasm. He continued to suck my clitoris whilst fingering me just inside my pussy and in no time I orgasmed again. My lover was still dressed, but I had felt his erection against my leg as he pleasured me, so I asked him to lay back and I undressed him. As I released his dick, it was about as big as my husbands, but it wasn’t my husbands, it was forbidden fruit, my forbidden fruit, and I’m sad to say that I sucked a cock for the first time in my life, and I sucked like it would be the last. As I sucked his cock, he reached around and started to rub my clit again, then he stuck two fingers in my pussy, and then one in my bum hole, and I orgasmed yet again and released his cock from my mouth. He rolled off the bed, walked around behind me, grabbed my hips and slid his cock all the way in, my first doggy, and god it felt good, I could feel his balls slapping my pillows and his pubic bone hit my arse. At that point I was liberated, I was being fucked properly, fucked like a fuck should be, for absolute pleasure. I orgasmed for the fourth time while he blew inside me and then I buried my face in the pillow and cried with joy and relief. I thanked him for giving me what I needed, and for recognizing it in me. I got dressed, did my makeup and walked out to catch a cab. I returned to my family with a sore and sticky pussy and a sense of accomplishment and less guilt than I would have imagined. I don’t believe my husband deserved to have his wife cheat, he’s a gods provider and father, but we were inexperienced.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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’d be surprised if I ever run into him (James) again and probably don’t want to. He’s a very nice person, very good looking and an attentive lover. He gave me pleasure like I’d had never experienced before and probably won’t again. It’s only been a couple of weeks, but I have masturbated to orgasm daily since. I told my husband that I had a dream ( not true) about inviting the postman in for a glass of water and I ended up sucking his dick. I wanted a reaction, that night we had sex and he pumped quite aggressively, so there was something there. I hope I can get him to lick my pussy and allow me to suck his cock, because I really don’t want to cheat again, but I do want to be fucked like a slut.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Attraction to partner(s), Learning new things, experimenting, To feel more confident

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

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? 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? It was naughty, dirty, slutty, lustful, liberating, freeing. I learned and experienced so much in one hour. To be pleasured, almost lovingly and fucked so aggressively, and to finally suck a cock.

What was the WORST thing about this hookup? Not being able to tell my husband. After I made up the dream about the postman, he was more aggressive in our sex, but nowhere near the point of me achieving an orgasm.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Random sex is not who I am, nor the people I associate with. I love my husband, but I wish he would lick my pussy, let me suck his dick, fuck me like I’m some random slut and occasionally stick a finger in my arse.

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? It was by far the best sexual experience of my life. Seriously I masturbate every day thinking about it.

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 hope this experience helps me make my husband a better lover and if it does give us both more pleasure, then my casual cheating session with have been worth it for both of us.

What do you think about the Casual Sex Project? It’s a great place to confess. I really needed to tell someone.

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