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What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Marketing
What’s your current relationship status? Engaged/Married (monogamous)
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? Horny 24/7
How many sexual partners have you had in your life (including oral sex)? 22
How many hookup stories have you here posted before? 0

My Second Married Woman!

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For less than a month

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? Kathy was a married MILF that was 4 years older than I with smallish B cup tits. She stood 5′ 10″ tall, which was nice because I am 6 inches taller then her. She was thick but not fat, great muscle tone. She also had a very sexy British accent that drove me around the bend and made me cum buckets, I’m a big man and she had a physique that could take a hard pounding and enjoy it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Kathy and I began chatting on a swingers/casual sex website. We chatted online for a week or two, discussing our sexual wants, needs, and preferences. The more we chatted, the more we both felt compelled to meet in person. We lined up a time to meet at a hotel bar in our city during the day as to not set off suspicions with her husband. We met over tea to see if we were physically compatible and how we got on in person. Our chemistry was great and we made the decision that we would hook up the following week at my house. She worked as a traveling salesperson and I worked shifts, so it didn’t raise many red flags. One thing we did discuss was if she requires me to have protection. In anticipation of our meeting, she began taking birth control pills. That told me that she was ready to get down with me and that she did have a fear of getting pregnant. I had been recently tested and she had only been with her husband for 15 years, so we had good histories. At the end of our meeting, I walked her to her vehicle, like a true gentleman. I gave her a tight hug and she felt my very hard penis press up against her. That turned her on and she asked for a kiss and we began to passionately kiss outside her car. She then told me that her husband’s penis was not as thick and that she was now very excited for our upcoming meeting. I was excited also and went home to masturbate and plan the upcoming session.

Kathy came over on a cold winter afternoon. She tended to her morning work appointments and then had me ‘booked in’ her calendar for the whole afternoon and had her assistant hold her calls. She also brought a bottle of nice champagne and two flutes so that we could have a nice drink before and after sex. I prepared the furniture in my rumpus room for various forms and positions of sex. I moved a small twin bed into the room, pulled the couch out a bit so I could bend her tall frame over it and set up a rocking chair and ottoman to lay her on her back and spread her legs like butterfly wings. I wanted her in positions where she would give herself to me and I could fulfill the sexual hunger that she had inside her.

This set the stage for 5 years of biweekly sex.

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? When Kathy arrived all bundled up from cold winter weather, I immediately took her downstairs. We kissed passionately and then I began to undress her. I got her fully naked and felt her up, starting to finger her pussy. It was wet and inviting. Kathy undressed me and we pressed our naked bodies up against each other. We then took a sip of champagne while naked and made a toast to us and the sex we were about to have. We polished off two quick flutes of champagne and then I laid her down on the chair and ottoman and asked her to spread her legs so that I could admire her well crafted pussy. She did just as she asked and opened up for my viewing pleasure. I began to eat and finger her pussy. Kathy was getting very wet and ready for penetration. At that time Kathy asked me to fuck her and I began to rub my bare cock against her pussy lips, as I wanted to feel her without any sort of barrier; I wanted the full experience. As a gentleman, I did ask Kathy if I could take a few strokes bare so that I could feel her from the inside. She agreed and I pushed in.

As I was fucking Kathy, she began to erupt into her first orgasm. Luckily I withstood her pussy squeezing and she came very hard. After she finished, I slowed down the strokes but did not leave her. It was then that I stated that I was not putting a condom on and that I felt that she was well enough protected, and asked her what she wanted; my bare cock and a big load of cum inside or a condom. She gave me the green light to cum inside her, as she wanted to feel my hot sperm inside, We kept going and Kathy started to orgasm again…as luck would have it, I was now ready to fill her with my seed. She bucked, writhed and contracted on my dick and had a massive orgasm, at which time I unloaded a large amount of sperm inside Kathy. I then pulled out and looked at my handiwork; her glorious, cum filled pussy. It was dripping out, down to her butt crack and onto the ottoman, which had a towel in case of this type of situation. Kathy’s face was all flushed and she was extremely happy.

We grabbed the flutes, finished the champagne and we went up to the bedroom. We got into bed and held each other, basking in the afterglow. She then grabbed my penis and began to stroke it. Kathy asked if she could suck my penis, as her husband wouldn’t let her do that; I enthusiastically said yes. Kathy then enjoyed giving me a blow job and got me nice and hard. Kathy then told me that I was to do what I wanted, as she wanted to make me happy. I asked her to get on all fours and get ready to be mounted. Her fantastic ass up in the air, I gave it a spank and then guided my dick into her slick pussy. We had a great session of doggy style, to which I blew another load into Kathy. We then got into the shower, washed the cum that was running down her leg off, felt each other up in the shower and then Kathy cleaned my cock off with her mouth.

Kathy was the best lover I have ever had. She and I broke it off, as she thought that I should find a nice woman to marry, which I did. Her love of my cum knew no bounds and even told me that if I knocked her up, she would keep the baby, regardless of her marriage.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? We both felt great and continued doing this one or twice a week for five years.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Power / Dominance

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? My brother who lived with me. He thought she was a nice lady.

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Kathy and her need for my cum inside her pussy.

What was the WORST thing about this hookup? Having it end

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It opened my mind to knowing that married women generally have relationships where the sex ends and it was nice that I could fill Kathy up with what she needed.

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!