Training My Sister-in-Law


What’s your gender? Man
How old are you? 64, 34 at time of story
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland, Ohio
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? retired attorney
What’s your current relationship status? Three women, one twenty years younger who serves me in an S&M relationship, the second a married friend in a sexless marriage in need of occasional comforting, and the third an interracial friend with expansive benefits.
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I am a dominant with spanking, corset, and leather fetishes
How many sexual partners have you had in your life (including oral sex)? I would guess between 60 and 80, perhaps. Perhaps slightly more. Less than 100, surely. I don’t know for sure, I don’t “keep score”.
How many hookup stories have you here posted before? 1

Training My Sister-in-Law

How long ago did this hookup happen? 30 years ago

What was your relationship status at the time? Engaged/Married (open)

How would you best classify this hookup? Short fling

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 partner was blonde, short hair, about 5’3″, 36D, attractive. Actually she was beautiful, like her sister, my wife. Good gene pool. Great legs. I knew her pretty well because she was my sister-in-law for more than 6 years at the time. I didn’t know her before I began dating my wife. I met her and got to know her through my wife and family gatherings. I always liked my sister-in-law, we hit it off as friends from the start and always had a nice rapport.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My sister-in-law had been married when I met her and through the first six years of my marriage. Then she divorced her husband. She had two young children at the time in elementary school and had been a stay at home mom but got a job selling jewelry at a department store. She was very lonely at night, so my wife began loaning her some of my sex books, which I didn’t mind. She really liked the Story of O, which my wife hadn’t liked at all and told her so. So my sister-in-law approached me privately about other S&M books I might have because she was consequently embarrassed to ask her sister for more. I passed her the Anne Rice Beauty series and some other titles as well as some fetish mags, like Secret and Marquis. She thought they were really hot and she told me she’d never before even imagined it but that she now fantasized about S&M a lot when she was alone. She knew I had an open relationship with my wife, of course, but I think she was only sharing this with me because we were quite good friends, not to be suggestive. And after all, under the circumstances, who else could she talk about this with? I tested her back with sexual suggestions (not involving me) and she blushed but answered all my questions and suggestions in the right way. It didn’t matter how personal I got, the fact that i asked made her have to answer, something I soon realized. I got her to tell me what most turned her on and what she fantasized about. I knew her schedule from my sister, so one morning I knew she was off work and her children were in school, I showed up at her door. She was very surprised but we were friends, I was her brother-in-law, she was curious why I was there but suspected nothing. Why should she? We had talked about my erotica, yes, but we’d never touched or kissed or had done anything inappropriate to our familial relationship. I sat on the couch while she fetched me a coke, then, when she handed it to me, I told her to step back one step from me and stand still. She did, looking at me strangely, still having no inkling of what was up. She was wearing athletic shorts and a t shirt, barefoot. I told her to take off her shorts and her panties in a calm but controlling voice.

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? My sister in law was visibly shocked. She just looked at me. We locked eyes. I said again, more firmly, “I told you to take off your shorts and panties. Do as your told or you’ll be punished.” She shuddered a bit, shocked, I think, by everything. She broke off the stare, looking down, blushing, clearly not sure about what to do. The she slowly pulled down her shorts and panties and stepped out of them, kicking them to the side. She looked back up at me, blushing and trembling. I told her to step closer to me. She hesitated for the briefest moment then took a step forward. She had lovely breasts encased in a support bra. I fondled her breasts through her shirt and bra, watching her face. She looked down but her nipples got so hard I could feel them even through the support bra. I grasped one as best I could through the bra’s heavy fabric, not too tightly and said, “Hard nipples. See how happy you are?” I reached down to her pussy and felt she was getting quite wet. I pulled my fingers out of her and swirled her juice between my thumb and forefinger. “See how much you like this?'” I said. I put my fingers in my mouth and licked them off slowly while she watched. I think she was relaxing a little, getting more turned on though still unsure, when I suddenly removed my fingers from my mouth and grasped her blonde pubic hair, tugging so I knew it would be somewhat unpleasant. “But what’s this? What is this shit? Why aren’t you clean and shaved? You’re totally undisciplined aren’t you? You need discipline don’t you?” She said nothing, so again I repeated myself. “You need discipline, don’t you?” Finally, she nodded. I grabbed her and twisted her across my lap and began spanking her. She was surprised and resisted, twisting at first, but I was much bigger and stronger and finally she gave up surrendered to me as I spanked her harder and harder. She began to sob. I stopped spanking her and she kind of slid off my knees down to the floor, still crying, her shoulders down, below my knees, very confused. I pulled her chin up and again looked her in the eye and told her I wasn’t done with her. I sat back and pulled out my cock, which was pretty hard by this point. She was kind of hunched up between my knees, glancing between my eyes and my cock. Finally she leaned forward and kissed my cock, then licked it and mouthed it, then began sucking it, stroking me, sucking and stroking until I came in her mouth. She took it all in her mouth and then rocked back so her ass was on her heels. I lifted up her chin as she stared at me. Finally, she swallowed it all. I pulled her up onto my lap and began kissing her, her neck, her face, her lips, her eyes and finally she kissed me back. “Remember, when you are good and obedient, it is very good and when you’re not…” We kissed and hugged for a bit and finally she hugged me tightly, pressing her face into my shoulder. “I can’t believe this,” she finally said, and then she kissed me rightly and firmly.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? When I left, she just stared at me, stunned I think. “No good bye?,” I asked. She still said nothing, I think just processing everything. After a moment’s silence, I said, “Well, no need for good byes because we’ve just begun.” And then I left. She still said nothing. I felt exhilarated at first and then began to worry because I didn’t know how she actually felt because of her silence. She was my sister in law, I liked her very much, and I did care how she felt. And of course if she reacted really really badly, there were clear ramifications for me. She told me later she was simply confused after that first time, confused and overwhelmed by it all, not even sure if she liked it or still liked me. Not hearing anything from her or my wife, I called her a couple of days later and she was a little distant, still deciding, still trying to figure it all out. It was a strange phone call. About a day later, she called me. I can’t believe that happened, she said. I can’t believe that happened to me. I asked if she was OK. She paused briefly and then said yeah, of course, I just can’t believe it actually actually happened to me. I asked her if she’d shaved yet and there was a dead silence. Finally she said no and there was another pause and then in a very soft voice she said she would that night. It was very clear she still had mixed emotions. It was also very clear she had deep needs. I told her good because she had a lot to learn, I had a lot to teach her. So she became my fantasy submissive and I her fantasy master, the first time in that kind of a relationship for either of us. Our relationship lasted about 8 months, very satisfying and fulfilling for us both, until she met another guy, whom she ultimately married. We never had sex again after she got married. I was very happy for her, a little disappointed at losing her service, but more happy than sad, certainly.. I always liked her. My wife died several years later and so my sister-in-law ended up she staying with me a couple of nights, to help cook and take care of the children as a kind of transition for me. She secretly slept with me those nights, very affectionately, but no sex. Loving kissing but no sex. God, she had such a beautiful body, it felt so good against me! Kissing, touching, but again, no sex. That was more than a decade ago. We don’t see each other often but we are still close. She’s such a great person! Her husband is a good friend of mine now, too. I presume he knows nothing of our sexual relationship but she and I have never talked about what happened after we stopped playing together. Nor do I know if she has a submissive relationship with him. If they do share such a relationship, which I doubt because her husband is fairly religious, they keep it well hidden. We do have a special bond, though, her and I, still. And on many levels, she was the best and the most favorite submissive I ever took, as well as my first.

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, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Power / Dominance

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? Not at all

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I’ve never talked to anyone about this except her while we were involved and not even her since her remarriage.

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? Getting close to my sister-in-law in a special way, discovering what a great person she was (though I always suspected as much), and learning about the practice of S&M together with a person I respected and trusted. She got to live a fantasy safely.

What was the WORST thing about this hookup? At this point I can’t say there was anything wrong with it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It confirmed to me that I was dominant and controlling and it freed me to explore those aspects again and again in many ways. I’d spanked other women before but in many ways this was my butterfly-emerging-from-the-coccoon sexual experience.

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 is now one of my fondest and most precious memories, both because it was so fulfilling and because I love my sister-in-law (though not as much as I loved my wife, who was also a wonderful wonderful woman, I might add). I don’t think my wife ever suspected. Even in an open marriage, I think my wife would have been threatened by this relationship, though she needn’t have been. We both loved my wife very much and wouldn’t want to hurt her or make her feel threatened or uncomfortable. It was just something very special between my sister-in-law and me. I share hoping other people can find something of value in the respect and caring we shared and showed each other in this relationship despite its S&M nature.

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? With the right attitude, caring casual sex is wonderful and fulfilling. It is not as good as a strong committed relationship but it can be a very nice thing. It has played a big role in my life. Certain of my sexual enthusiasms were not shared by my wife, including S&M. Without casual sex, without my wife always looking the other way when I wandered, my marriage wouldn’t have been nearly as successful. As for society, I think if the values of casual sex would be generally acknowledged and accepted, if people could understand and accept the difference between responsible play and genuine commitment, people would learn to enjoy more loving and responsible casual sex.

What do you think about the Casual Sex Project? If it teaches an attitude that casual sex can and should be loving and responsible, it could do a great thing. I like reading others stories, though sometimes I think the participants don’t fully get it. Then again, who am I to judge?

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