Ok, here's the situation. We're all very married with no intention of leaving any of our spouses.... This part is clear. We're also all over 50, we've all been married for over 30 years and it appears we're all just looking to enhance on what we feel is missing in our current long term marriages. I'm older than both of the sisters, but lets just say I take very good care of my body. I lift free weights about 3 hours a weeks, cardio everyday and at 6'1" 195# I'm very fit. So I do get a lot of attention from women even though I'm married. Back to the original question, which sister do I date? I've screwed this up before by asking one roommate out only to find out later the other roommate was really much more interested in me. Given they are married, I'll start slow with just going for coffee. But I'm afraid I'll ask the wrong one. Any rational constructive advice is appreciated. Thanks,
Ok you haven't told us anything about either one of these sisters. Am I supposed to pick the one on the left?
Good response. Ok, both are very attractive, blond, slender, very fit. I'd say the younger of the two is mid 50s about 5'5" probably 125# in all the right places, blue eyes. A little shy and sort of slow in denial about her desire to have a lover outside of her marriage. Yet, once she started thinking about it, it became much more interesting to her. Her older sister, I'm guessing 2 years older is a little taller, about 5'7" probably the same weight. So she's a bit slenderer. She's quite outgoing and seems very interested in engaging others in conversations. Probably "in my opinion" slightly more attractive. I suspect the younger of the two just might be more of a pleaser as a partner and the older of the two might be more interested in being pleased. I very much like to please a woman in an intimate environment.
And of course, about 5 minutes after I talked with the two sisters this morning, a widowed woman I'd never met before came up to me and introduced herself. Based on her smile, eye contact and body posture she clearly is interested in getting to know me better. Her husband passed away 2 years ago. She's a good looking brunette about 65 years old. Both sisters were watching her chat me up.
Let me get this straight. Your married. The sisters are married but not related to you in any way. All three of you wish to enhance your sex lives. Your planning an affair but don't know which sister you would rather do it with. You want the best experience out of this because it didn't work out that way before. And now you have another interest pining for attention. Is that about it? Here's my thought. According to your posts in other threads you have acquired a lot of experience with sex outside of marriage. (Swinging, swapping, and the like) Use it. Don't go slow and fool around with dating or coffee. Come right to the point. If all three of you already know that you want to get together for sex do so. Set up a tryst with one and then the other. Unless, that is, they would be receptive to meeting with you for sex together. Either way if you get with both of them and have sex you don't have to worry about whether one is better than the other. You will know. But know this, they will get together and compare notes. Oh, and don't forget the 65 year old widow. She may be looking for a mercy fuck.
Yes you understand the situation pretty well. You might be right. My style is to tend to go slower with a married woman who's doing this for the first time as I suspect she might bolt.
Cold feet are always a possibility. But with two married sisters and a widow who are showing interest the chances of one or all backing off are slim. Depending on how close the siblings are could set the tone for their interest. If they are being competitive it may play well into your hands, and believe me being sisters they talk. If they show any emotions because you are interested in the widow this could also play well. I'm curious as to where the contact is taking place. My first thought is at your local gym or another gathering place where membership is required. Keep to your style if it has worked in the past. I might suggest showing interest in the widow with the sisters present, or without as you choose, to see their reaction. Follow up with the widow and meeting her to see where it may lead. That might pull the sisters to become more aggressive and lower any inhibitions or obstacles about any outside of marriage sex. Besides, if this is occurring at a gym or other like gathering spot it is likely the three of them, two sisters and widow, may start a innocent conversation. (If you know what I mean).
Met all three at the gym. I'd say the sisters are quite close, they just got back from a week in Cabo (without husbands). I'm sure the two of them have discussed me, clearly the interest is pretty high coming from the pair of them. Just not sure which sister is most interested.
The plot thickens. So, the sisters are close and vacation together. Alone with no spouses in tow. It might be one or both hooked up while in Cabo. Warm sun, soft sand, beautiful ocean. Enticing circumstances. They may be more experienced than you know. I take it you aren't really interested in the widow. I would understand as juggling all three might be to much. You still might use her to get the sisters competitive juices flowing.
I just met the widow. I've known and talked with the sisters off and on for about a month or so. My gym days haven't always been the same as the sisters. Working on changing that a bit to get more face time.
Face time is good. This scenario intrigues me. Please keep me informed of your progress. I would like to know if my suspicions are correct about play by either one of the sisters, or both, during the trip to Cabo. Their husbands may or may not be involved or aware of anything. On the other hand they may be open to their wives explorations. As a side note I am wondering where your wife fits into the picture. I am, much like yourself, married to a wonderful woman with no intention of leaving. I've been walking this planet over 60 years and have been married to her for over 40. We stayed mostly monogamous while having a torrid sex life together. It's been just in the last several years I have explored outside with consent. She has been beset with many medical issues that makes sex very difficult and painful, she would rather be celibate. I accept her position and find other avenues for my sexual needs. Based on review of other posts you have made I suspect your wife is rather open about sexual pleasures. If you don't wish to share in this open forum feel free to PM me. I would like to know the outcome of this.
I don't mind sharing most info on here. It sounds like the two of us have some things in common. My wife in recent years has had health issues as well that make sex difficult/painful. My wife fatigues easily these days, we'll play 9 holes of golf and she's spent for the rest of the day. Most days an afternoon nap helps her recharge a bit. That doesn't change the level of intimacy we share. We've been together 42 years. I likely won't see the sisters till next Wednesday at the earliest.
We do have some things in common. My wife has had health issues that makes sex very painful for the last several years. Nothing we have tried medically has worked. We are sexless but so compatible in all other ways. There is no way we will separate, ever, until death takes it's toll. I have consent to fulfill my desires which I do occasionally.
My wife cracked me up yesterday. We went to an art fair and while we were there I told my wife that a woman "chatted me up" pretty good. She said "Yea I saw that have fun, but today you're going home with me". We both laughed. Later I figured out that we were talking about two different women. And honestly one of the artist we bought a painting from locked onto my eyes and just didn't let go. She asked me for my contact info. Who knows maybe it was just "marketing" on her part. But damn she was good looking, fit and yes a very very good artist. What a fun day. Picked up four nice pieces of art and hopefully I'll convince my wife to let me add a sculpture piece by a Japanese artist that I really liked. Might be a bit of a budget buster. We'll see.
