Loading...The “cleanest” sexual relationship I’ve had was also, in the end, the kinkiest. I lived in a cabin up in Vermont for a short time several years ago. I’d just moved east from California, had a couple bucks in the bank, and was woodshedding some songs for a new album.
First night there I’d pulled all the curtains off the windows and stuck the clock radio in the closet, so every morning I woke up to the impossible shimmer of sunlight off the lake and got right to work.
I’d stop for lunch and a workout or bike ride, then do some more writing until it got dark. Some nights I went into town to the only bar open in the off-season, some nights I went right to bed and started the whole thing again the next day. It was a very present-tense existence, if a little lonely. But lonely was the point.
One night in town I struck up a conversation with a liberal-looking couple in their 30s who had sat down next to me at the bar. She was blonde and taller than I was, slate-blue homemade tattoos intermittently visible under her sleeves. Remnants, I guessed, of a wild teenhood.
He was funny and unpretentious, and I soon found out that he ran a fleet of fishing boats up in Maine. The business had been successful enough to allow them homes and cabins in several states, plus a “cruiser”–e.g., a yacht–that they took around the world several times a year. One of their cabins, it turned out, was on the same lake as mine there in town.
We left with open invitations to each other’s pads, and a few days later I headed their way instead of into town for my afternoon break. I knocked on the door and someone else answered–a dark-skinned, doe-eyed post-college-age young woman who smiled warmly and said, “Hi, who are you?”
I told her I’d made a mistake, that I was looking for Jan and Dave. I explained who I was–renting the cabin just around the curve of the lake, closer to the town road, etc. She said that no, in fact I had the right place, that she was a renter too, and that Dave and Jan only came to town once every few weeks and stayed in the second bedroom. She said her name was Gwen. “So what’s your story, what are you doing here?” she asked.
I told her about the album, and it turned out she was a jazz singer on break from a graduate program at Brown, in Rhode Island. She’d just ended a relationship and wanted to shed some old skin. We sat on her porch by the lake and talked through the afternoon. I was massively impressed with her–she was challenging and political and informed, and she had a charming way of leaning toward me when I spoke, so as to get all the words into her ears before she considered and responded. We left with a date to continue the conversation in town the next evening.
I’ll be honest: I went home and jerked off thinking about her. Her honeyed skin, that warm smile, her small, almost boyish body. I pictured how her face might look from below as I went down on her, and how her pussy might feel as I fucked her from behind, there by the lake, both of us feeling the breeze and each other’s body. I wondered if she liked it rough. I wanted her.
We met the next night, and talked our way through seafood and wine, then through a walk around the squares and avenues of the small central district. Then, hand in hand now, we headed back to the lake. We reached my cabin and Gwen invited herself in to hear a song or two.
I lit the candles that I’d been using as nighttime light. We both sat at the piano bench and I played her one of my new songs on the electric keyboard. She listened intently, again leaning in to take everything in through her ears. The second time I got to the chorus, she hummed a harmony part. Then she stopped me. “No, it wants to go like this,” she said, and sang a different melody. “Try that.” I did. She was right. I hated her and loved her for it. Then she sang “Motherless Child” while I played for her. When it ended, she put her hand on top of mine, intertwined our fingers, and kissed my cheek light as a whisper.
I turned to kiss her and she smiled. “We should talk,” she said. We did. The relationship she’d just ended, she told me, had been with a woman. In fact, all her relationships had been with women. “Oh, you’re a lesbian, that’s OK” I said, pretending not to be disappointed. She said she didn’t like labels. I told her that whatever she was was fine with me, in case she thought I’d be judgmental about it. She said that wasn’t it.
“I watched you,” she said. I didn’t know what she meant. “I came over last night to bring you this”–she fished a book about hikes in the area out of her bag and handed it to me. “And when I got close, I saw you. On the couch.”
I could hardly pretend I didn’t know what she meant now. She’d seen me jerking off. I told her that, funny enough, it was her I was thinking about. She looked flattered, of all things. I said, “That seems kind of ironic now, right?”
She said, “No, that’s the thing. I liked it. I liked what I saw. It turned me on.”
Interesting, I thought. I had a crazy thought, and figured there was nothing to lose at this point by voicing it: “Would you like to watch me again?” I asked. I studied her eyes for any offense. There was none apparent. She didn’t hesitate. “Yes,” she said, her voice a bit softer.
I took her hand, and sat her in one of the soft living room armchairs. I brought the candles over to the living room table, then turned the other armchair to face her.
I let my mind go off into a fantasy, this one involving Jan, from the couple from the bar. I pictured Dave fucking her from behind while she looked up at me, rubbing me through the front of my jeans. I rubbed myself through my pants, there in my living room, while Gwen watched my hand.
I pictured her unzipping me, lowering my pants. I pulled my pants off in real life. I pictured Jan stroking me, and began stroking myself. I kept eye contact with Gwen, who was taking it all in through her eyes the way she took conversation in through her ears. I noticed that her skin tone had begun to change a bit. She watched my hand stroke my cock, looked down at my balls, followed my body up to my face, studied me, caught my eye, gave me that beaming smile of hers, then watched my hands some more.
Her hips rocked subtly in the chair.
Now in my fantasy, Dave was gone, and I was fucking Jan from behind while she went down on Gwen. I closed my eyes to savor that thought. When I opened them, Gwen’s hand was down her pants, and her fingers were making little rhythmic undulations against the front of her jeans. Her face was flushed, but she was still watching me. She made eye contact again, gave me a smile, but it was a little wilder this time, her eyes both more intense and less focused.
I pictured Jan kissing her, working her fingers in and out of Gwen, while I fucked Jan. I pictured leaning forward and kissing Gwen as well, feeling my motion into Jan reverberate into Gwen through Jan’s fingers. This put me close to the edge. Between heavy breaths, I said to (the real) Gwen, “Is it OK if I cum?”
Her breath was choppy and quick. “Do whatever you normally do,” she said, her eyes narrowing intensely as she answered. She didn’t close her mouth when she was done speaking. Her hands were really going to town beneath her jeans.
I pictured tall blond Jan nestled up behind small dark Gwen, arms wrapped around her, kissing her, holding her for me while I moved deep into Gwen’s pussy now. I pictured kissing Gwen while Jan whispered, “That’s it sweet girl. Are you ready for him to cum in you?”
“Yes,” Gwen said, both in my fantasy and in real life, watching me. My head buckled forward and I sprayed shot after shot of cum onto my chest and belly. I tried to keep my eyes open for as many of the spasms as I could so I could watch Gwen watching me, but it was an intense orgasm. She stopped moving her fingers and just studied me cumming–her mouth still open, her eyes still slightly wild.
When the spasms stopped, she got up quietly and returned with a towel. She knelt next to me and wiped me off. It was gentle and intimate. When she finished, she simply rested her head on my chest and lay there in silence for a very long time. I lay my hand on her and she again entwined her fingers with mine.
Finally she lifted her head, kissed me gently on the lips, and said, “Thank you. That was lovely.” I got dressed and walked her to the door. “I can’t tell you where it goes from here, until I do some thinking,” she said. “But how’s dinner Friday either way?” I said Friday was fine. She took my hands, looked me in the eye, gave me another blast of sunshine, and headed off.
Dinner Friday was a homemade meal at her place. Afterward, we made out for the first time, in the crisp air of her porch. She sat down in one of the chairs, looked at my crotch, and said, “Show me again.” I leaned back against the railing and faced her, stroking myself off while she slipped her skirt up and rubbed her unshaven but fine-haired pussy. When I was close to cumming, I asked if she wanted to make it cum. She nodded. I stood close to her as she grasped me and perfectly matched my natural rhythm–she really had studied me. She watched me until my eyes started to roll back a bit, then studied my cock as she stroked the cum out of it, feeling my balls contract with her other hand.
When it was over, I bent to kiss her, then slipped a hand up between her legs. She held my wrist and and stopped me, just long enough to say, “No penetration, OK, D___?” I said it was fine, then held her to me as I rubbed her to orgasm. She put her lips next to my ear so I could hear her breath surging as she came.
We kissed again and I spent the night. She told me about an early sexual assault by a man, that that’s why she didn’t like the label “lesbian” but also didn’t trust men physically. I told her that whatever she needed was fine with me. Thus began several weeks of an affair based on mutual self-pleasure and non-penetrative contact. And, oddly, It was the most intimate sexual relationship I’ve ever had.
For a time. It hit a wall after three weeks or so, where we both began to understand the limitations of the arrangement. “Eventually, you’re going to want to fuck me,” she said, correctly. “And if I’m honest, I’m never going to want that.” We agreed to a few days of solo contemplation.
I laid low, finished up some tunes, stayed out of town. Three days later, Gwen knocks at the door.
“Do you love me?” she asks. I say I do. “I love you too. Do you trust me?” I say I do. “Good. Then follow me. By the way,” she says, a couple of steps later, then turns around and finishes the sentence with a long, deep tender kiss.
She leads me to her place. A silver Range Rover sits outside. We go in, and Jan is there. “Hiya, D___,” she says, smiling. Gwen sits me down.
“Jan came back Thursday,” Gwen starts. “Did you know that we used to go out? That was before Dave.” They smile at each other like only long-time female friends can. “So, I’m talking to her. About you. And us.”
I look back and forth between them.
“Here’s the thing. There is one way it could work.” They share yet another look. “What if you went out with me and fucked Jan?” Now it was my turn to lean in.
“You heard me,” she said, correct again. “I’d be your lover, only you’d fuck me by fucking Jan. I’d be there, of course. It was Jan’s idea, if you were wondering. It turns me on, D____, and I’m not just saying that. I’d be into it. It might be a way…”
Silence while they watched me take it in.
“And…” She waited for me to show that I was ready to hear more.
“There’s something else we could do. Jan’s not always around. I need to come to grips with the idea of penetration if I’m going to be with you.” I waited. “There is a way that we could perhaps have penetrative sex.” I perked up further, mind still wrapping itself around the first part of the arrangement.
“The only catch is…” She looked at Jan one more time. Jan smiled knowingly. “It would be me penetrating you,” Gwen finished, pulling a strap-on dildo from her bag and holding it up for me.
Yikes. A cock in my ass. That wasn’t where I thought this was heading. She read it on my face.
“It’s up to you, D_____. I’m the last one to force penetration on anyone. But I thought, maybe, it might help me, might give us a shot. Otherwise…”
I looked at Jan. She turned very deliberately, looked Gwen up and down slowly, then back at me, as if to say, you’d really give that up just to protect your dumb male macho pride?
Again, I figured there was nothing to lose. I walked over to Gwen and kissed her. Looked her straight in the eye. “Fuck me,” I said. “right now. Put that on. Let’s do it.”
She literally screamed in delight and anticipation. We all crawled out of our clothes, Jan acting as facilitator for both of us first, then removing her own. She had a lithe, athletic body, dotted here and there with those slate-blue tattoos, including three perfect circles in an arc just above her pussy.
She saw me staring.
“It’s this,” she said, indicating the three of us. “It’s three, the perfect circle. A circle of circles. Around this” –indicating her pussy–“the origin of life. I love this one. Dave did it.” She pulled the skin back to give herself a better view of her own tattoo.
We all closed in on one another and, arms around each other, began kissing. Jan turned Gwen to face me and ran her hands down our backs as we kissed and swayed. She snuck behind Gwen and nibbled at her shoulder, kissed down her back. Then she came to me, cupped my ass in her hands, bit the back of my neck. Gwen and I had our hands together, moving so that my hardening cock pressed against her clit from below. It was like the beginning of all love-sex, except that we both knew that something different lay ahead.
When she felt me fully hard, she broke our kiss, found Jan’s hand and brought the taller woman over to take Gwen’s place in front of me. She kissed me as she “gave” me to Jan. Then she backed away to watch.
Jan and I shared a brief smile, then got very quickly down to business. We kissed deeply. She was taller than me, so she could rub her clit up and down the length of the underside of my cock with a simple graceful bend of her knees. She reached down and stroked my cock. I flicked a finger across her clit, then slipped it inside her. Her body slackened. She was wet. She immediately began riding my finger. I slipped another inside and fucked her with my hand. Her breathing immediately turned shallow, began to include whispy traces of her voice.
Looked for Gwen. She was leaned back against a table, legs spread, one hand rubbing her clit, the other cupping a small breast, mouth open, head canted toward us with that same sexy-studious look that won me over all those weeks ago on her porch.
Jan maneuvered herself off my fingers and literally led me by my cock to the couch. She lay back, rubbed me against her, put the head of my cock against her pussy lips, then called Gwen over. “I want you to see,” she said. Gwen knelt next to us. “You watching?” Jan asked. Gwen nodded. Jan wriggled her hips and rode me all the way up into her. She lowered her hips again to let me almost all the way out, then rode me back in. She ground against me while I was all the way in, let a little air escape from her throat, then again lowered her hips.
“Do you want to feel it going in?” she asked Gwen. Gwen reached toward us and wrapped her fingers around my cock, right where the head was resting inside Jan’s wet pussy.
Jan pushed up again, letting Gwen feel the lips move all the way down my cock, until once more I was sunk all the way into her. “It’s nice, right?” Jan asked. “It’s nice,” Gwen nodded. She looked at me. “You do whatever you would normally do. This is fine with me. This part is for you. I mean it.” I kissed her, then looked at Jan.
“Let’s get down, baby” I said, and we both laughed. Then kissed. Then fucked hard. She pushed her hands against the end of the couch and spread herself wide, legs back, to open herself for me. I drove down into her. She pushed back against each stroke. Her hands stroked my ass and back, her legs played against my sides and hips. She stuck the back of one foot down into the crack of my ass and laughed. I got my thumb between us and rubbed her clit. She brought her hand down to hold it right where it was, rocked her hips hard to meet me, and, saying “oh yeah, oh yeah, oh yeah,” using her legs to piston against me, then gritting her teeth with sexy intensity, came.
She sat halfway up, kissed me deeply with one arm around my neck, the other off the end of the couch, moving. I looked back and saw why. Gwen had the strap-on on, kneeling next to us. It rose sexily out of her boyish body. Jan was helping her rub lubrication on it. Gwen rubbed one palm in sensual circles over my ass, the other hand covering Jan’s as it stroked the fake cock.
Jan extricated herself from beneath me. She smiled at me. “OK, big guy. Ready or not, it’s your turn.” I looked at Gwen. She gave me a very intimate look. “Whatever you’re comfortable with, D_____. We don’t have to do this. If you want me to stop at any time, just tell me, OK?” I reached over to touch her face, kissed her. “I know,” I said. “I love you. Now please shut up and fuck me in the ass.” Laughs again.
Jan made her way to the other side of Gwen, to facilitate once more. I got on my elbows and knees, ass up in the air, cock still hard from having been inside Jan without cumming.
Gwen put lubrication on her hand and knelt with her face close to mine, stroking my cock. Jan squeezed lube onto her fingers and spread my ass cheeks, rubbing first around the outside of the hole, then poking her finger just inside me. Gwen watched me, tenderly and co-conspiratorily, for my reaction. I flicked at her lips with my tongue. She did the same back to me.
Jan began slipping the first two knuckles of her middle finger gently into my asshole, getting it ready. Gwen saw my face change, felt me freeze up a bit. She looked at my as if to say, “everything cool?” “It is,” I said. “Just different.”
“OK, sweetheart,” Jan said, “I’m ready for you back here.”
Gwen squeezed my cock a couple of times, checked once more for my reaction, then practically squealed as she quickly got up and moved behind me on the couch. Jan put a bit more lube on the strap-on, then placed the head against my asshole. “Move into him slow,” she said. “Once you’re in to about here, just hold on and let him get used to it. D____, you’ll let her know when she can go on from there.”
“Will do,” I said, then looked back over my shoulder at Gwen, who looked unexpectedly sexy kneeling behind me with a cock pushed against my ass.
“Whenever you’re ready, sweetie,” she said to Gwen. Jan held my ass cheeks apart as Gwen pushed in. Too big, I thought. No way I’m doing this. Holy shit.
She pushed farther. “Good girl,” Jan said. “Hold it there.”
It frankly hurt, and as Jan saw my cock start to soften, she reached under for it, stroked it smoothly. That felt good, and I noticed things had started to ease up in back as well, open up and relax.
I turned around and nodded to Gwen. She smiled. Jan pushed her a bit farther in, stroking my cock with her other hand. Gwen took hold of my hips for leverage, pushed in farther. Jan rubbed my ass, my back, massaged my shoulders, reached back under and pulled at my cock again. She leaned forward and flicked her tongue against my earlobe. Gwen pushed in farther and I felt the base of the strap-on push against my ass. I grunted.
“How you doin’ big guy” Jan asked.
I thought about it. “It’s too big. It’s too deep. It’s not comfortable. And…I don’t mind it at all. Go for it, baby,” I said to Gwen.
She laughed, held my hips, and began fucking me, slowly pulling out and pushing back in. Jan slipped in front of me, held my head in her hands, kissed me, cradled me, reached under me to stroke me some more. I could feel that my cock was unusually swollen and rock hard, could feel my balls swaying as Gwen fucked into me. Jan reached down further and let my balls brush against her open palm every time they moved forward in response to another thrust from Gwen.
And I hated to admit it, but things felt pretty good up in my ass. The rhythm and the texture of the dildo itself were sensual in their own way. And after years of the being the one doing the fucking, it was profoundly interesting to get fucked.
I turned around to Gwen and said, “this is fun.” She beamed, laughed, said “I know!”, then leaned forward to rest her head against my back as she fucked me. It was a very sweet moment, given that she was fucking my ass with a fake cock attached to her.
Jan was now on her back on the couch, legs facing away from me, playing with herself, her head just below mine. I kissed her lips, then her neck, then reached forward for her breasts. She sidled farther under me, I took a nipple into my mouth, between my teeth. She reached back above her head and took my cock with both hands. She moved again and I kissed farther down her body. Finally her sweet tattooed pussy was below me. I sucked her clit up into my mouth, flicked my tongue against it, buried my head between her legs. I couldn’t help but smile at this strange perversion of my original fantasy of fucking Jan from behind as she went down on Gwen.
Jan moved her head from side to side, running her tongue across my balls with each pass. She stroked my cock with both hands, getting them wet with her own saliva every few strokes.
Then Gwen’s rhythm started to break a little, and I looked back to see Jan’s fingers up under the strap-on, working on Gwen’s clit.
But now I was hooked. I pushed back against the strap on, fucking it with my ass the way Jan had fucked me with her grinding pussy. Jan was stroking me with one hand, licking my balls with her tongue, getting Gwen off with her other hand. Ever the facilitator. Gwen had starting writhing her hips, which put the strap-on in all sorts of new angles inside me.
I could tell Gwen was going to cum, and I knew sure as hell I was about to. I wanted to hold off and do it with Gwen. Jan was a smart one. She reached up, took Gwen’s hand, wrapped it around my cock, helped her stroke me. She worked Gwen’s clit expertly and got her to start bucking and gasping. As Gwen came, Jan kept Gwen’s hand rubbing my cock, stroking the cum out of me as well, my balls resting in Jan’s hot mouth, spray after spray squeezing from the head of my cock, my ass trying to tighten but finding a cock there instead. I let out a primal grunt. Another. It felt like I was about to pass a tennis ball through my cock. I’d never dropped such a big load, and it felt like it wanted to just keep coming.
Finally, her orgasm over, Gwen collapsed on top of me. She ran her hands softly up and down my sides and ass. She kissed my back. Jan worked her way from under me and helped Gwen out of my ass. I lay on my stomach, Gwen lay on top of me, the strap-on resting against my crack, as my own cock had done with others on so many occasions. And then, in bit of circularity so lovely that I’d leave it out if it weren’t true, Jan went and got a towel and wiped us all down.
So that’s how the sweetest sex I’ve ever had also became the kinkiest. Sex between Gwen and me, if it went beyond touching and watching, became Gwen fucking my ass, me fucking Jan in front of Gwen. Sometimes Dave joined us, sometimes he didn’t. When he did, it was a before-and-after thing, where he waited until the three of us had done our thing and then attended to Jan one-one-one, often right there in front of us, sometimes back in their cabin if we were in mine.
The inevitable eventually happened, of course, Gwen had to go back to school, I had to leave for the city. We knew that was it. We said a long, sweet goodbye, naked body to naked body. There were tears, wine, and deep sensuality. But no penetration–of either of us. That seemed right to us, and was.
I sing that song “her” way now, recorded it that way, and think of her whenever I do. I wonder if she thinks of me when she hears it.