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What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Education
What’s your current relationship status? Married and Complicated
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)? 5
How many hookup stories have you here posted before? 4

Sister in Law and More

How long ago did this hookup happen? On and Off

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

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

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? Lauren is tall, 5 foot 8 inches, blonde with shoulder length hair, brown eyes, thin, with long skinny legs. I have known Lauren since before I dated and married my wife, I actually dated Lauren before my wife, who is her sister. Lauren and I are different, the old notion is that opposites attract. She is high energy, always in motion. I like to take my time and enjoy life and the flowers on the way. I have always liked her and felt an attraction for her that I have kept under wraps. Lauren is 47 now.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Lauren and I have been hooking up for some time now. I’ve shared a couple on here already. It seems the sex ebbs and flows as Lauren’s energy and time commitments ebb and flows. Our schedules are crazy at times and other times far more open. We are sexual together during the slower times. She prefers that I come to her house when everyone is gone during the day and she is off work.

This time Lauren called me and we engaged in catch up talk, having not touched base for a month or so. After getting caught up on her adult kids and my adult kids, Lauren asked what I was doing the next day. I told her I could be available and she asked if I could come to her house at 8:00 a.m. Sure.

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 arrived at 7:55 a.m. and parked down the street and walked to Lauren’s house. I didn’t have to knock as she opened the door allowing me in and then shut and locked it. She was in her lingerie and her beautifully large 40D breasts were easily in total view. I love breasts and my hand went to massaging them as our mouths locked and our tongues eagerly danced together in our mouths.

After a good 5 minutes of me feeling her breasts and making out, Lauren led me up the stairs, undressed me, and led me to her bed. I could have led her to it as we have made love now many times on that bed. On the bed was a dildo and I opened up my eyes wide for a minute. “You’ll see” she said sitting on the bed. I could tell the dildo was lubed up very well and as I undressed her, she kissed me again and began to stroke my dick.

“Lick my pussy” Lauren ordered me, and guided my head down to in between her knees which she spread. I kissed her pussy lips and her clit. Lauren was already soaked in anticipation of our sex. I roused her vagina and her clit and brought her to orgasm. She now rolled over on her stomach and picked up the dildo and said “gently fuck my ass with it.” I had never done this and I knew that Lauren had never done this and it excited both of us. I took the dildo now and rubbed it around her asshole and then slowly inserted it. Slowly I drove it in and slightly out and back in, keep up that motion. Soon Lauren’s ass was moving in a small circular motion as I drove the dildo in and up her ass slowly. “Yeah, Oh yeah” she moaned. I saw a condom and the tube of lube on the bed and I stopped for a moment, put on the condom, something we don’t use, and lubed myself up. I put the dildo aside and my dick was bigger than that anyway, and I inserted my condom covered dick into her anus.

Lauren moaned as I gently drove my dick in and back out of her anus, in and partial out, and back in and partially out, and back in. Again and again I screwed her ass until I felt her body tensing, her ass raised in the air, and I drove hard and deep into it making Lauren scream with pleasure. Four or five times I drove my dick up her ass and each time she moaned or screamed in pleasure. Lauren collapsed as her body now relaxed from her orgasm, and she rolled onto her back. Her hand went to my dick and removed the condom and in the missionary position, she guided my dick into her hungry, wet, wanting vagina.

Lauren moaned again as I entered her. I used only the tip of my penis head at first to enter her, teasing and enticing her. “Give all of it to me NOW” Lauren commanded. I did just that slowly driving my dick all the way up inside of her vagina to where I could tell it reached her cervix. Then slowly I withdrew until only my penis head was in her, and then drove deep again, all the way, and out to just my dick head was in her. I kept this up as a constant motion, in and out, in and out, Lauren moaning “Oh Yeah” or “Yes, Yes Oh Yes” or “Uhm, Uhm, so good” or just ‘Uhm” over and over. Her tits were hard as a rock, her mouth eagerly kissing me, as she thrust her tongue inside of my mouth.

As we continued to make love, Lauren wrapped her legs around my ass and hips, rubbing them with her feet as we made love. I was not sure why, but I felt no urge to cum and I was rock hard and ready to go for a long time that day. I kept making love to Lauren, and told her “I love you” which I do. She held me closer and stuck her tongue in my ear and said “I love you to.” We kissed and kept making love as I watched her chest turn red, and it spread up her neck and into her cheeks. “I love your dick in me” Lauren said, breathing heavier as I kept up the motion.

By now her eyes were closed, her body was tensing again and then exploded into multiple orgasms. I kept making love to her as her legs fell off my ass and hips and her arms fell to her side. “More, I want more, oh yeah, go.” Lauren told me. So I did. I kept making love to her, watching her, holding her eyes in mine as I kept making love to her. I didn’t go faster, I didn’t slow down, I just kept that constant in and out motion going, driving deep, withdrawing to leave just my penis head in her vagina and then driving deep again.

I could tell she was drying out a little and asked if she wanted lube. “No, just go.” Lauren replied. Slowly she got wet again. It had taken me 15 minutes of oral sex to make her orgasm the first time. 20 minutes of anal sex to make her orgasm and 25 wonderful minutes of intercourse to give her clitoral and vagina orgasms from my hard dick. We had been making love for an hour and I wondered how much more we both could go.

I withdrew now from Lauren, still rocked hard, and she did lube her vagina up a little. We now moved to where Lauren laid on her side, one leg straight, the other fully bent at the knee and her arm bent at the elbow for support. I was between her legs so that my right leg was slightly bent and was laying next to the straight leg of Lauren. My other one is on the woman’s lap of bent legs, and I penetrated into her from behind. I propped myself up with my arms, one was near the back and the other on Lauren’s breast feeling it, massaging it, playing with her erect nipple. This allowed us to continue to french kiss and for Lauren to use one hand to feel my dick going in and out of her vagina. That turned her on.

Now slowly I made love to Lauren, our eyes expressing our sexual hunger and our love for each other. I worked myself up, thrusting in and out of her wonderful pussy as we stared into each other’s eyes as we made out and made love. We had looked up this new position online and found with our own adaptation that we REALLY enjoyed it, it was very intimate. Lauren whispered in my ear “I want your baby, cum in me. Fill me up.” That turned me on though at 47 I doubted that Lauren would get pregnant.

Faster I went now, deeper, longer, only withdrawing my dick about half way out of her vagina. Lauren moaned in pleasure as she and I stepped up the pace. In and out, faster and faster. I could feel the my dick getting ready to ejaculate and I knew Lauren was close. I wanted us to cum together so I paced it and told Lauren to yell when she was going to cum and I’d cum with her. Laurent thrust my dick rapidly in and out, deep and deeper inside that wonderful vagina and screamed “NOW!” I released at the exact moment Lauren’s body relaxed as she experienced her orgasms and I ejaculated multiple times deep in her.

She held me tightly, using her vagina to milk my still hard dick. We kissed and kept kissing and Lauren said “I am in love with you.” I smiled and said “Not just my dick?” “Well, that too, but that’s part of you.” After ten minutes of kissing and milking my dick for all of its cum, we laid side by side kissing and talking.

I asked her if she really wanted another baby. She said no, not really but she would take it if it came but since I had had a vasectomy she knew it probably wouldn’t happen. She explained that she wished she could have had some of my babies. I looked at her and said “Well, that probably isn’t going to happen, but we can sure practice and see if it will!” Lauren smiled, kissing me, her hands touching my balls, my hands rubbing her vagina as I sucked her boobs.

We made love again, this time Lauren rode me and we went for a good 40 minutes before Lauren had another orgasm and I ejaculated in her again. After that Lauren wanted to try the missionary position with her legs on my shoulders and I penetrating her vagina, my hands rubbing her breasts and her hands rubbing my thighs. This allowed for real deep penetration by my dick inside her vagina and she really loved that, again having multiple orgasms as I had multiple ejaculations in her.

By 4:00pm we were done, and we took a shower together. In the shower as is our custom now, I knelt on my knees, my lower legs bent behind me, and Lauren sat down on me like on a chair, driving my hard dick again inside of her as I fondled her breasts and nipples, kissing her neck as she leaned back slightly and she rubbed my thighs. Loved this new position and that is what Lauren and I love about being on-going lovers, we are willing to try new things and discuss them and enjoy them.

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? As is typical for the last week I have seen Lauren everyday and we plan to keep it up for at least another week. Lauren says after two weeks of sex together, she needs a week or two off to recover for our next go around. Some days we meet and its just for an hour and a half lunch make love session. We try twice a week to make love for the whole day while everyone is gone. Lauren has told me she has cut her husband off from sex, saying as she enters menopause, it is hurting. He bought it though she will give him a blow job twice a month to keep him content, and the fact that he is the father of her children and she cares and loves him. He just cannot satisfy her sexually as we do when we make love. So no plans to leave our spouses, and we are fine being lovers. Lauren asked me after we made love this morning if I ever would make love to her and my wife (her sister) in a three some at the same time? That would be interesting I told her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, It was easy / convenient, I love making love to Lauren

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? 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? Not at all

What was the BEST thing about this hookup? Sex is outstanding, the best I have ever had. The emotional connection is intense and heightens the sex. Lauren is a soul partner as is her sister, my wife. I am a lucky man to make love to both.

What was the WORST thing about this hookup? Like NOTHING.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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? Next story will either be how we did it like teenagers in a car, or in a camper.

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? Nothing really.

What do you think about the Casual Sex Project? Interesting.

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