Smiles of a Summer’s Night



What’s your gender? Man
How old are you? 64 now, 56 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? happily retired
What’s your current relationship status? I have a submissive who I allow to serve me four or so days a week, a married mistress who is a granny in a sexless marriage, and an interracial friendship 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? 2

Smiles of a Summer’s Night

How long ago did this hookup happen? 8 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 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? I knew her casually but not very well. Her husband played on the same adult softball team as I did before meeting his wife and her husband and one of their sons was in an Indian Guides tribe with me and my son, which is when I first met her. My late wife became friends with her but they weren’t particularly close. As for her appearance, she was once slim and attractive but by the time of this story she had thicker thighs, a largish round ass, still nice breasts, maybe 38C, still a pretty face, a lot of smile lines because she smiles a lot and makes everyone else smile, too. She was kind of a comfortable overstuffed easy chair of a woman (and she’d smile her lovely smile if she read those words). Handsome, though, definitely a handsome woman. Whenever she smiled, as she often did, you couldn’t help but smile back. Before we hooked up I certainly liked her, I’d always had fun with her, she was very nice and nurturing but I can’t say that I knew her well. I was better friends with her husband and her son from Indian Guides than I was with her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, we were out on one of the islands in Lake Erie where one of the other Indian Guide dads had a vacation cottage. A nine bedroom “cottage”. It was an Indian Guide reunion kind of thing four of us dads did almost every summer. The boys were all then just turning 21 and full of vinegar. There were the 4 parent bedrooms on the top two floors and the boys divvied up the rest of the bedrooms between themselves. (There were also 2 daughters there who shared a room.) Em’s husband (her name was Emily) wasn’t there yet, he was to come on the next morning’s ferry. He’d had to work the night before. It was after dark, so maybe 9:30 or a little later. Em and I were in the cottage, everyone else was down at the pier, swimming and partying. There were also some other people from some of the other cottages (i.e., teen/twentyish bikini girls) as well as other adults there and the music was loud enough that we could hear it clearly at the cottage. We were both in swim suits, like everyone else, but neither of us were much inclined to go to the pier. We were drinking coffee and laughing, we had a nice rapport, telling each other how we really didn’t want to go to the pier, but there was nothing to do otherwise. We were talking and over her shoulder I could see a nautical chart of the island and the parts of Lake Erie in the immediate vicinity. And I suddenly remembered the time years ago we (the Indian Guide dads) took the boys wading to the next islet over, across about a three-eighths of a mile channel at a spot where the water didn’t get much more than 5 feet deep. “Hey, you know what? Let’s go on an adventure!” She smiled, of course, and asked me what I meant. I told her to grab a blanket and follow me. She was game and a good sport, so off we went. We had to walk for maybe 25 minutes to get to the channel shoals, during which time we had a delightful conversation about everything and nothing at all. When we got to the point I knew the shoals started, I put the blanket on my head and got into the water, which was probably 4 feet deep there. “What are we doing here?” she asked, looking around. The closest thing in sight was the island trash dump maybe 500 feet away from us. There was no beach and seemingly no point to getting into the water there. “Trust me and just get in,” I said. So she did, smiling at the pleasant sensation of the warm water shallows. “Ohhh”, she said. So I began walking out into the lake toward, apparently, nothing because it was dark, the moon had not yet risen, and the islet itself was pretty flat. “What are we doing?” “Trust me,” I said, “it’s an adventure.” Em was and is game, so on we went and soon the islet came into view. We walked ashore onto a small stony beach. There was a small rise and then a grassy field. That’s it, a maybe 2 and a half acre grassy field flanked on the leeward side by a small stony beach, the whole islet. She looked around. “Why are we here?” “You’ll see.” I spread the blanket out and laid out on it. She sat near me. I said, “No, lay on your back and look up.” She did and said “Oh, my!” See, we were city folk used to a city sky but out here in the middle of the lake, with no lights around, geez, the stars were just TREMENDOUS! The whole Milky Way spread out across the sky, not just the thousands of stars we were used to in the city but trillions and trillions of stars, like a frozen fireworks display. “”I’m 52 and I have never seen the stars like this,” she said. “See,” I said. “An adventure.”

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? We were laying there, looking up at the stars, talking about everything, just everything, my childhood, her childhood, my late wife, whom she’d very much admired, things we’d each done and seen in our lives. It was very nice, not at all sexual, just pleasant. But as we lay there, wet from wading through the lake, and with a steady breeze coming off the lake, she began to get cold. I told her to roll up in the blanket, which she did as best she could with me lying on it, too, which didn’t completely cover her and brought her into close proximity to me. So we were lying very close, looking at each other, happy and relaxed, I couldn’t help noticing how beautiful her eyes were and I told her so. And of course she smiled and thanked me. and we kind of laid there looking at each other for a few moments. And then, spontaneously, I kissed her. And she sighed and kissed me back until she realized what she was doing, and then the look on her face! “What are you doing? I’m married! To one of your friends!!! And I knew your wife!,” as if that mattered, since my wife had been dead for 5 years at that time. But it mattered to her in some female way that us guys never seem to understand. I apologized. I told her I was sorry she was so beautiful on such a beautiful night in such a beautiful place under such a beautiful sky. She just looked at me and then (as always) she couldn’t help but smile. “What kind of apology is that?” “A sincere one,” I said, which made her smile even more. I looked at her and said, “I’m sorry but I’m going to have to apologize again,” and I kissed her again. It wasn’t planned, it just seemed right. Necessary, almost. She kind of pulled away and got up on her elbow. “Is this supposed to be your adventure?” she asked breathily. “No,” I said, “the adventure was coming out here. This, this is…” And I didn’t know what to say. Finally I said, “beauty.” She was clearly shaken. “You may remember that I am a married woman, Mr. Felix,” she said. “I do remember, Em. But if my wife were alive and sitting back at the cottage right this moment, I still would have kissed you and kissed you again and those kisses would still not be enough. Sometimes life happens.” “Please don’t do this!” “OK, OK, but you know as well as I do that you kissed me back both times.” At that, she sank down again to the blanket, staring into my eyes. We lay there for a moment and I kissed her again. She didn’t resist or struggle, but after that kiss she said, “I’m too old for this, I’m an old woman.” “Just as I’m an even older man,” I said, kissing her again. This time she didn’t resist. This time she definitely kissed me back. I laid back from her and raised my hand so she could see it. She stared at it, dumbly. I slowly slowly reached over to her and placed my hand on her inner upper thigh, my thumb and forefinger pressed to the still wet crotch of her one piece swimsuit. “Oh my god,” she said. Isn’t that what they always say? I kissed her again. “All you have to say is ‘no’,” I said. I slipped the shoulder straps of her swimsuit off her lovely shoulders. She was breathing heavily but she didn’t say anything. “All you have to say is ‘No”,” I repeated as I pulled her swimsuit down to expose her lovely ripe breasts. She still didn’t say anything. She just looked away. And then her suit was off and I kissed her again and again. And then my suit was off. She never said no. It was as simple and as straightforward as it is possible to have sex, missionary, me on top. And then me lying beside her. It was as simple and beautiful as the night sky spread out above us. We laid there together for maybe an hour, hardly talking. She saw a shooting star. We had to get back, everyone would be wondering where we were. So we got dressed, we waded and walked back, her with the blanket wrapped around her because she felt chilly in the night air. Everyone was in the living room when we got back and everyone stared at us. “Where were you two?” by this time it was almost 2 in the morning. “We walked to the winery (which was at the opposite end of the island from where we actually were and a much longer walk), closed it out (it closed at 11pm) and I got us a bottle of wine, which we drank on the pier there, watching the lights of Put In Bay. We were talking. She asked me about Kathy (my dead wife, which she had) and talked about so many things (which we also had). We finished the bottle of wine and we walked back.” When I mentioned talking about Kathy, who everyone had liked and admired, suddenly the subject got changed and they started talking about something that had happened at the pier where they were swimming. Em excused herself and went up to bed. I guess the wine had given her a headache–or so she said. I talked with my son and a couple of the boys for a minute, we all laughed, then I went to bed, as did the rest of the parents who were still up. Within another half an hour everyone had gone to bed and the house got quiet. About 4am I had to pee, which I did (damn senior bladder!). My bedroom was on one side of the third floor bathroom, Em’s was immediately adjacent on the other side. The house was dead quiet. I opened Em’s door. She was asleep–or, at least, she seemed to be. I stood over her, just looking at her. I was about to leave again when, I don’t know why, maybe I made a sound or something, she for some reason suddenly opened her eyes. She looked at me. “Are you there or am I dreaming,” she said. I paused for a heartbeat and said, “No, I’m here. I don’t know why, I just wanted to look at you.” “Well, my god, we’re not alone on an island anymore. Leave!” I didn’t move. I was frozen. I put my hand on her cheek. We locked eyes. Finally she said, “OK, but only for a few minutes.” She threw open the single sheet she had over herself. I crawled in. I held her and we kissed. “I can’t believe we’re doing this, that I’m doing this,” she said. “Can you please take off your nightgown?” It was mid-calf length, white cotton. “You are absolutely incorrigible and unbelievable!” she said. She laid there for a minute looking at me and then smiled and shook her head. Sher had a wonderful smile. She shrugged off the nightgown. Skin to skin. We kissed some more and I began to finger her. She quickly grabbed my hand. “I’m an old woman, I have a little trouble lubricating, after the island I’m afraid I’m done tonight. And without lube, your fingers hurt.” Now I was embarrassed. We kissed some more and hugged and then, after a bit, “But I can do this for you.” And she bent over and took my cock in her mouth, kind of sitting on her haunches. I said, “No, wait.” I pulled her hips over to my head and kissed her pudendum. “I have plenty of lube in my mouth.” So we sixty-nined until I came in her mouth. I don’t know if she came, but I doubt it. Then she laid in my arms again and I held her. She said, “You know we’re too old and too fat and too unattractive for this, don’t you?” “I may be too unattractive but you are nothing but beautiful.” She smiled that killer smile of hers again and said, “Butter wouldn’t melt on your tongue, now would it?” We laid in each other’s arms until about a quarter to 6, when all the birds started raising their pre-dawn ruckus, indicating the sun would soon be up. She was dozing. I slipped out of the bed and slipped my shorts back on. I kissed her on the cheek and said, “Sweet dreams, Beautiful.” She never opened her eyes but she smiled. And I went back to my room. Everyone was still asleep.

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? When I finally got up, it was after noon. They were all eating lunch, so I guess it was OK timing on my part. Jerry, Em’s husband had arrived on the 10am ferry. He was sitting at the kitchen table drinking a beer with Em, who had a white wine spritzer. “Well hello Sleeping Beauty!” Jerry said with a big smile. “How the hell are you?” “I’m good, Big Guy. When did you get in? Hey, Em.” She looked at me for maybe a second too long, then at her husband, “I guess I’ll let you two lovebirds bill and coo,” she said, clearing their lunch dishes and walking to the front porch where everyone else still eating lunch were still sitting with her wine spritzer in hand. I spent more time the rest of the weekend with Jerry and the guys more than with Em and was never alone with her. Of course Jerry slept with her. We all went back together on the same ferry. I was sitting on the passenger deck with just about everyone else except for Em. Where was she? I went down to the lower level, the car deck, to the end of the boat, where she was standing, alone, looking back at the island. I walked over and stood next to her. “A penny for your thoughts,” I said. She glanced at me and then back over the rail. “What was the name of that island that we waded to?” “I don’t know,” I said. We stood in silence for a minute or two, both of us lost in thought, looking back at the islands. “It was Nowhere Island where nothing ever really happens,” she said. “What about back at the cottage later that night, does nothing real ever happen there, too?” She glanced up at me again but didn’t say anything, then looked out across the water. “Something happened, Em.” She looked at me yet again, longer this time, but still said nothing. She reached over to the rail, put her hand on mine and squeezed. Then she turned away from the water and began walking back toward the passenger cabin. When she was about five feet away from me, she said, “I’m married.” She had tears in her eyes. She went back up to the passenger cabin. I looked over the water, straining to see Nowhere Island. But how can you see Nowhere?

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection

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? Somewhat

Did your partner(s) consent to this hookup? Guarded/guilty consent

To whom did you talk about the hookup? How did they react? No one except Em herself.

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing was Em. She was the very best thing. She had a wonderful smile. Thank god she still smiles on me. She is loving and stalwart and still somewhat happily married to my obese diabetic impotent friend Jerry. They now have separate bedrooms. Her pubic hair is now completely shaven and her pud is clean, just the way I like it. For the past almost eight years she has, off and on, been my loved and loving paramour. Sometimes she feels too guilty and she must stop for a bit. But that is happening less and less often. And she’s always come back.

What was the WORST thing about this hookup? The six weeks after the island, thinking about her, telling myself how irrational I was being, how stupid, she was married and she was a good woman, it was nice and let it go, before she finally called me again. Guilt. Feeling guilty about coveting my friend’s wife. Not really my friend, not my close friend, but yeah, still, a friend.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? As I was setting this all out, I was at first sure I was writing about casual sex and it was casual, supposedly one-off sex out there on the island. But now, over the years, it has mellowed into something real and important. She is married and I have other sexual partners (which she knows about) and Em and I are unlikely to ever get together together in that love and marriage way (though I suppose that could someday happen), but even if we never get together, this is an important relationship for both of us. Maybe the most important relationship to both of us now. Yeah, me and that comfy overstuffed chair of a woman Em.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? Did I mention Em’s wonderful smile? The hardest thing is not being able to now tell my friends how much I care about Em. Sometimes that really does hurt. Birthdays, holidays can be tough. We make our own holidays alone. I think the necessary secrecy hurts her in the same way. We don’t want to hurt anyone else, we’d just like to be able to socialize together, to be public without hurting anyone. I also wish Jerry wasn’t such a good decent guy. That’s why good, decent Em still loves him and why he still deserves her love.

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? Casual sex has sustained me over the years. As for society, I understand commitment but there is room for good honest commitment-free but otherwise responsible casual sex as well.

What do you think about the Casual Sex Project? I hope it helps people. I hope people read it for understanding themselves and their feelings and aspirations as much as for titillation.

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