Shared Orgasm and Fisting Firsts: Two True Stories

a lightly edited Girl Boner Radio transcript

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Suzannah’s story

Suzannah:

So I was 25 years old, and I had never had an orgasm with a partner. And I had just gone on vacation in Ibiza and met this amazing man who lived in Germany. And I invited him afterwards to come visit me in New York. And I decided that this was going to be the day that I had my first orgasm with a partner. 

August (narration):

That’s Suzannah Weiss, a certified sex educator and sex and love coach and writer. She told me that the idea of experiencing orgasm with a partner had been on her mind a lot at that time. She’d been writing about sex and relationships and had access to resources, so it seemed within reach. 

Suzannah:  

So I did a lot of things to prepare for that I did a hypnosis session focused on overcoming sexual issues. I took a course on female orgasm, and I learned to be determined and to do whatever it took. 

August (narration):

At first, it was awkward—before anything sexual began. It was summertime and her would-be sex partner showed up at her New York apartment. [door knocks, door opening] They had planned a vacation. During it, she hoped her partnered orgasm would happen.

Suzannah:  

And it was quite awkward at first because we had only really known each other for a few days on this vacation. But then it was like we had known each other forever.

August (narration):

They started out spending time together, exploring the city. 

Suzannah:  

He had never been to the US. So I showed him around. I took him to Grand Central Station and Central Park. And we got lost in the park and we kissed outside the – I forget what it’s called, that place in Central Park with the boats. And it was very romantic. 

August (narration):

That night, they took a shower together. 

[shower running]

Suzannah:  

And it was super hot… Then he fingered me, but internally, which wasn’t gonna lead to an orgasm. And I kind of knew that, but I just went with it because I was enjoying it anyway. 

[soft moan]

August (narration):

The next day, they worked side by side at a cafe then returned to her apartment where things got steamy again. And this time, she met her goal. 

In a story Suzannah wrote about this experience called “My First Shared Orgasm,” for the anthology, The Big Book of Orgasms, Volume 2, edited by Rachel Kramer Bussel, she wrote: 

“The pressure builds up in my clit again, rising and falling. I’m starting to feel embarrassed about all the false alarms. But then, it rises again — and it doesn’t fail this time… I finally release your arm as orgasmic waves undulate through me, laughing with bliss and relief… I tilt my head up and smile and kiss you. You don’t know I’ve just reached a milestone.”

August:  

What was it that eventually did bring you over that edge, do you think?

Suzannah: 

I think the first thing was believing it was possible just having that curiosity of ‘oh, maybe this could actually happen this time.’ Part of it was the way that he was fingering me. He was focusing on my clitoris as opposed to internally, which doesn’t do as much for me. 

He was a really nice guy. And I could tell he was really wanting to give me pleasure and wasn’t judging me in any way. And that he would do whatever it took as well. 

I had remembered what I learned in the course on female orgasm that I had taken that week. And some of the suggestions were to fantasize if you need to, to not worry about how much time it took. And to move your body in ways that made it more pleasurable for you… I remember sort of grinding my hips against his finger. And for some reason, spreading my legs really wide was helping open up the sensation. 

And instead of just giving up, I think because a I had taken that course and have this idea of empowerment in me and also because he seemed like someone who would be open and who would want to give me pleasure however he could, I think I just felt like I had permission to ask for what I needed and do whatever I needed.

August (narration):

On her way to that climax, she let her mind wander and fantasize. In one, she’s masturbating with a group of women on top of a mountain; they join in harmonious moans.

[African drum/tribal music, sounds of birds chirping/mountain air and a chorus of moans]

Suzannah:

I think I conjured up that fantasy after reading about Betty Dodson’s groups and how the women would masturbate together and this feeling of sisterhood. And I think something about that was appealing to me. So that was my go-to fantasy at the time. And I really wanted to push myself over the edge. So I was like, ‘okay, I’ll go to the fantasy that usually works.’

August  

I love it, up the orgasm mountain. That’s awesome. 

And when the orgasm actually happened, was it different from orgasms you’d had on your own?

Suzannah:  

I remember feeling really surprised that it actually happened. I kept feeling like I got close, but then it wouldn’t happen. So then when it actually did, I was just like, Whoa, I just did that. And I remember feeling this rush of endorphins and this feeling of closeness with my partner, and just this surge of self esteem and confidence that like, ‘Oh, I can do this. I am normal.’

August:  

And then it happened again.

Suzannah:  

Yeah, that was surprising. So then once I realized I could have one, then I had three because I was just like, ‘Okay, I guess if I keep going like this is actually possible, I might as well just keep trying.’ And I felt so good afterward.

August:  

Oh, that’s so good. Did you ever tell your partner that those were your first with a partner?

Suzannah:  

It’s funny, I didn’t. I had too much shame over it. And I wanted him to think that I had always been this sexually self actualized. And he never knew this three years we were together. He actually never knew that. I think because I had this – I had built up this image of myself as a sex writer and someone who has really sexually competent. And for some reason, that information just seemed like it would paint me in a negative light. And so I never told him. 

August (narration):

Some of that shame showed up in the ways she perceived her experience. Near the end of her story about it, she wrote, ”I’m elated to know that I’m not broken.” And while she knows she wasn’t in fact broken before, that’s exactly how she felt after those shared orgasms: not broken. 

If you relate to those “before” feelings, Suzannah wants you to know that your challenges aren’t your fault.

August (narration):

Do you have any insight or advice for somebody who’s in that place where they feel broken because they aren’t experiencing partnered orgasms?

Suzannah: 

Yeah, I would say that if you’re not experiencing the sex life that you want right now, that doesn’t mean your body is incapable of it. There have been studies showing that when women who have never had an orgasm are taught how to orgasm, the majority learn within a few weeks to orgasm both alone and with a partner. 

And we have to keep in mind that this is a society-wide issue that the pleasure of people with vulvas is valued below those with penises and our definition of sex accordingly prioritizes intercourse which is often the way that those with penises, but not those with vulvas orgasm. 

August (narration):

She pointed out that there are many reasons behind orgasm challenges.

Suzannah:  

Sexual trauma can be a reason, body shame, sexual shame, and lack of exploration, because it’s discouraged. So it’s important to look at those external factors. I know that the problem isn’t your body, unless there’s a health condition in which case the problem may have to do with your body, but can still be worked on. And so it’s really not you, and there are many people who thought they could never enjoy sex and now have like the most beautiful sex life. I know myself that from working on that I got a sex life that was better than I ever thought I could have. So it is possible for you, too.

[acoustic, encouraging music]

August (narration):

You know what else can help put you over the edge, alone or with a partner? Sex toys. If you love clit play, or good vibes on other erogenous zones on the outside of your body – your nipples, your thighs, your back – head to thepleasurechest.com to explore their Wanderful World collection of sensual wand massagers. You can also transform your wand into an internal G or P-spot toy by adding an attachment. Head to thepleasurechest.com to learn more and start shopping. Again that’s The Pleasure Chest at thepleasurechest.com. 

[acoustic, encouraging music]

Judy’s story

August (narration):

Now for a true story about another first: fisting. 

Judy Calabrese is a writer and performer, who describes herself as pretty crunchy—meaning into all-things-natural. Crunchy like granola. Which is why when she gave birth to her last child in 2013, she opted for an unassisted home birth. Just she, her partner Chris and her doula were there. And it was with this doula that she would have one of the most surprising sexual experiences of her life. 

For the sake of privacy, let’s call that doula Reza. And to Judy, Reza was more than a doula. 

Judy:

And she was instrumental in being my pregnancy assistant. Aside from just my birth assistant, she was my best friend. We traveled the whole road of pregnancy together. We had done a birth worker training together for half a year, which was super intense, we got really close. And we were in love with the world of birth. Everything about birth was exciting to us. So when it was time for me to give birth, I leaned on her emotionally, spiritually, and physically, a lot. 

August (narration):

That baby was Judy’s third. She was 43 when she gave birth—and at a point in her life when she felt “extremely powerful.”

Judy:

And choosing an unassisted birth was a big part of that feeling of power. I just knew I could do it. I knew it’s what I wanted. I knew it was illogical. But it was a truly intuitive decision. And I just felt and knew that I needed to bring in this being this soul needed to come in this way. 

August (narration):

When the time came for her baby to emerge, she was in her bedroom with Chris and Reza. 

Judy:  

She was the first person I saw after he was birthed. I looked up, and there she was, and it was like, everything’s gonna be okay. Just looking at her face. 

My partner was there in the tub with me… It was his first child, he was completely freaked out. Present, but like there for the baby and making sure I was okay. And she was just there for me. And there was something so profoundly beautiful about our connection and our friendship and this sort of uber-human thing that I was doing um that just bonded us on a level that was just beyond even friendship. It was like sort of cosmic. 

August (narration):

Nearly three years later, after Judy’s home birth, that they reconnected. During those years, Reza had had a child of her own, which involved a traumatic birth experience — the complete opposite of Judy’s, she said. And for a while they’d lost touch because of Reza’s postpartum depression.

Judy:  

She went through a really hard time. And so when we got together again, as friends, she was going through a divorce with her wife. She was a single parent. I mean, her life had gone upside down in the three years since I had really seen her. 

August (narration):

And Judy had missed her. On top of the close friendship and shared experiences and passion for birth, Judy had always sensed something more about their relationship – a spark they barely acknowledged.

Judy:  

She and I had always had pretty extreme sexual chemistry. And I was very cautious about engaging that energy at all. 

August (narration):

For one thing, Judy’s a good amount older than Reza. And, while Judy was very open about her open relationship with Chris and her fluid desires, Reza seemed more private.

But then one day, Reza showed up on Judy’s doorstep, displaying a very different vibe. And she had some news.

Judy:

And when she arrives at my house, completely drunk one afternoon telling me like, “me and my wife are getting divorced and my life is over, but I feel really happy and good, but my life is over,” we rejoined one another in a very different form. 

Now it’s like, you have a baby, I have a baby. We haven’t seen each other in over two years, almost three years, and now you’re going through a divorce. 

Me and my partner were still in an open relationship. I had shared with him all of the desire that I had had for her but didn’t know what to do with. 

August (narration):

One day, Reza was sitting at Judy’s kitchen table—clutching her first smartphone. Judy couldn’t believe it.

Judy:  

Talk about crunchy. She’s way crunchier than me. She’d never had a cell phone. She lived without a TV. She lives in a cabin. 

And here she is at my house with her smartphone, and she’s talking to me, scrolling. I was like, “What are you doing?” She’s like, “Oh, I’m on Tinder.” I was like, “Woah, you have a smartphone, and you’re on Tinder.” Okay.

She’s like, “Yeah, it’s great.” And I’m like, “So you’re dating?” And all of a sudden my heartbeat starts to race. And I realized she’s out there dating people. It was some primal thing like, I didn’t even get a chance. You know? [laughs]

August:  

Aww…

Judy: 

Yeah. And it was so it was primal. It was this really deep pull inside of me. And she was like, “Yeah, I haven’t really met anybody yet. But I’m open. It’s amazing. I’m single for the first time in 10 years,” and blah, blah, blah. 

I have a history with things happening – my unconscious sort of wakes up in these very strange moments. And out of my mouth, I say to her, “I would fuck you anytime.” 

She was completely shocked. And then she kind of broke into this little smile. And she was like, “You mean that?” And I said, “I do.” And then it was sort of game on.

August (narration):

Game on. But the sex didn’t happen immediately, which ended up making it that much hotter. 

Judy wrote about her experience in a story called “Cave Walls,” also for The Big Book of Orgasms, Volume 2,. In it, she talks about boundaries Reza set up. A lot of that started via text. Judy wrote:

“Language is foreplay, you texted. Where do you like to be touched? Everywhere, I replied, as if I had never been asked before.”

Judy:  

We had a whole three days of texting, back and forth. And she had all these rules that she needed me to follow. 

And at first, I bristled at the whole rule following thing like, oh, how much do we have to talk about this? But then when she addressed me as a top, my entire being just like melted. 

August (narration):

A top, meaning Reza took the reins. Judy was more the “bottom,” or submissive.

Judy:

And I really liked it. And I was like, I was just putty. I was like, “Y’all do whatever you want me to do now?” And it was a game changer for me. I don’t think I had ever submitted on that level before where body-mind-spirit was just a complete yes.

August:

I love that you had this primal experience you’re talking about this just primal kind of heat. And it sounds like you were taken aback a bit by this boundary/rules discussion and then it turned into this really deep primal unfolding. Was your arousal just building through all of this?

Judy: 

Yeah. I had never realized that boundaries could be so hot. It just never occurred to me. And the more boundaries she set down, the hotter it got. 

So it was like she really dictated her world to me. And she did it in such a deft and sultry way that it made me want to yield to her.

August:

Do you remember a specific rule or boundary that was particularly hot to you?

Judy:  

I mean, the first one was you won’t touch my pussy unless I tell you to. 

August (narration):

Then there were specific ways Judy was to address Reza. If Reza texted Judy a question—“would you like it if I did blank to your blank,” and Judy responded with simply, “yes,” Reza would correct her: that’s “Yes please.”

Judy:

And I would text back, “yes, please.” 

And the tighter the parameters became the hotter I got.

August (narration):

What Judy didn’t expect was that these steamy text exchanges would lead to her being fisted for the first time. 

Judy: 

Yeah, I had no idea. Like, none. 

I had been with several women before. I’ve been bisexual all my life. I mean, I’ve identified as bisexual since I was a teenager. um

I’ve had many different sexual experiences with women. And I think what my idea of fisting was was like someone punching your vagina. I mean, really. I didn’t think about it too much. It just was like, why would I do that? 

And then when I, you know, realized what fisting really was, I still thought why would someone want to do that? It didn’t really cross my mind. And if she would have said, “Hey, come over, I want to fist you,” I would have been like, “No, sorry, I’ll take a raincheck.” Like, I’m I wasn’t going there for that. I just really wanted her. I wanted to explore whatever sexual experiences we were gonna co create. And that’s what I was in it for. 

August (narration):

The whole experience happened at Reza’s place.

Judy:

My heartbeat was racing by the moment I got to the door. I mean, even driving there I was already so turned on. I remember buying a bottle of wine to bring to her and just feeling like it was like a first date and I was a teenager. It was so nerve wracking and exciting and new.

I walked in and the first thing I said was, “It’s so clean in here.” She has a kid, I have a kid. I’ve many kids. So I thought ‘How did you get it so clean in here?’ And then that arousal of like she cleaned up for me. That immediate thing, and her house was sort of on a hill and it looked out to the Blue Ridge Mountains [nature sounds] where we live, but it’s not really very common that you get that view and I was saying things about the landscape. It was as if we were really on a date. Like I hadn’t known her for years. It was suddenly a charged space where every breath felt metered.

And she’s like, “Can I get you some wine?” and we started drinking wine and then suddenly we were already two different people, like in this charged space of like, we had already decided: we are here to have sex. [match being lit] That was it. Those are the parameters: We are here to have sex. It doesn’t have to mean anything. It doesn’t have to go anywhere. This is what we want. 

And we sat on the couch, we didn’t even make small talk. We just sort of stared at each other. [laughs] And she said, “May I kiss you?” And she leaned over and kissed me and um started kissing my mouth, we made out for a really long time. And then she started kissing my neck. And that’s when she said, May I bite you?” 

[sexy rhythmic music]

When she sunk her teeth into my neck it was a completely animal experience where I, again, my body just yielded. Almost like prey, you know, I just gave over to that bite. And I felt it melt down to my feet, like as if I was sinking into the couch. 

And we did this sort of making out on the couch, ripping off each other’s clothes is really hot and sweaty, tangle of hair and groping for each other. And so it went really fast. It was hot and passionate quickly. 

[music crescendos then fades out]

Judy:

I have this thing that I let go of that night, which is there are limits to sex with women. I really believed that. I’ve I said, I’ve always been a bisexual woman. I’ve had most of my long term relationships, though, with men. And I really enjoy sex with men. And I have enjoyed sex with women, but not as much as I have enjoyed sex with men up until that point. 

And she just showed me things I did not know were possible, you know? Like, she must have bitten and sucked on my neck forever. And it was light. It was deeper. It was really rough. It was really soft. She was licking up and down my neck and my jaw bone and my ears and she was kissing my face for a long, long time. 

There was no getting anywhere. We didn’t have a destination. And that’s what made it so it’s what made it so eternal and so beautiful. We were just on this road, I did not know where we were going. 

And every time she placed a new hand somewhere on my shoulder and pushed my shoulder back and then moved my head aside so she could bite the other part of my neck or lick me or put her hand to my throat. It was like I was happy being there forever.

August (narration):

And then Reza said something that would bring that newness to a whole new level: “May I put a finger inside you?” Judy: “Yes, please.”

Judy: 

And let me tell you something you think ‘one finger, who cares,’ right? Oh my god, I felt every centimeter enter me. She did it really slow. And she would run her fingers down my labia first, over and over again. And then after a long time of like, massaging my labia she said “May I put a finger inside of you?”  There was like a whole world, just in her stroking her two fingers down my labia.

And I did not know for a long time that I was going to be fisted. I just was enjoying the journey of her fingers inside of me. And my first sensation was ‘Why didn’t it ever feel like this before?’ When she had three fingers inside of me and then four fingers inside of me, it felt like the inside of me was expanding. 

As if, like I write in the story, there were places where she was going and I didn’t know were there. And I didn’t know exactly what that meant in terms of anatomy. But I was like, why does this feel so different? And it was very gentle, but very firm. And it was this like, experience of what part of my body is that? I didn’t know. I was like, Okay, well, that could be my cervix or kind of feels like she’s over by my ovaries. But that’s not actually possible. You know, is my uterus expanding? 

I didn’t know what was happening because I couldn’t imagine – I couldn’t imagine the reality of what was happening. I was just trying to ride the waves of pleasure. And at one point, I think she tried to open her fingers inside of me, the four fingers, and there was this, [gasps] like this catching my breath of “Oh…” like almost a little bit of worry… I grew babies inside me technically, of course, I could get that big inside of me. But what’s happening? And there was that little edge of fear. 

And I just trusted my breath, and I trusted her and our kissing and our sweaty bodies and our moving together. And she’s like grinding her pubic bone on my leg. And it was just so hot. It was just this wild dance that was happening. 

And then at one point, she must have put all five fingers inside of me because I remember her sort of gasping and just going like, “Oh, Judy.” And I was almost – like that too high up on the swing feeling, like what was happening? What do you mean? Was there something wrong?  [laughs]

I felt like I was in a state of freefall. And when I was fully cognizant of the fact that she had all five fingers inside of me after she sort of breathed my name in this exhale like “oh Judy,” and I was like, oh my God, her entire hand’s inside of me now, how is that possible? 

I mean, I’m not gonna say I left my body. I was fully in my body. But there was also this sort of, almost like this astral body part of me that was bigger than my human body. And it felt like there was something energetic about the expansiveness of her entire hand inside of me. Not just, ‘Oh, my vagina is stretched to this extent.’ It was some energetic, almost like a portal of going beyond what I thought was my limit. 

And there was pain involved, but it wasn’t acute pain. It wasn’t the kind of pain where I was like, ‘How do I bear this?’ It was like, this pain that had a reason for it, as if my body was giving me permission to go beyond some limitation of pleasure and say, “Look what you can do. Look how much more there is.”

August:  

That sounds really intense, and, and powerful.

Judy:  

It was really, it was really intense. I was shaking. My whole body was shaking, which is really interesting, because after I give birth – I’ve had three babies all at home – we shake. There’s like a hormonal reaction after you give birth, where you shake pretty uncontrollably. And it felt like that. 

It felt like she had reached the place, like I say, in the piece, that only my babies knew. 

And it was like, showing me, just for me, that part of me that only my babies knew. But here I am revisiting it for only pleasure. So it was like a piece of me returned to me that I didn’t even know I had lost. And I was like, ‘Wow, look at this! [Look at] This whole new other frontier inside of me, how amazing.’

[acoustic, encouraging music]

August (narration):

If you’re thinking, holy smokes – Judy and Reza must have needed some serious chill time following all of that – well, same. Some relaxing TLC together would’ve been nice. Unfortunately, that is not what happened. 

August: 

It sounds to me like, because your sexual experience that you had with this friend and doula, that it was so intense that there was probably some aftercare involved. How did things happen/unfold after?

Judy: 

It was actually a disaster. [laughs]

August:

Oh no! 

Judy:  

Which I have been reflecting on for a good part of six years. My personal take on it is that we broke through the ceiling of pleasure that night. Those are actual words that she spoke to me: “Sex with you is like a sacrament.” And that is not to make myself so amazing. It’s that that’s what it was. It was a spiritual experience for both of us. 

I don’t think she had ever had that before. I certainly had never had that experience before. She had also never fisted anyone before. So it was new for both of us. And I don’t know this to be true, because I never spoke to her again. She cut all ties from me. And the only thing that my heart tells me is she couldn’t allow that version of pleasure to be part of her life, or at least part of her relationship with me.

August:  

Oh, that sounds painful.

Judy:  

That was really hard. It was really, really painful. Because I realized through the experience that I loved her so deeply. So deeply. And wanted her to be my partner. um And I had spoken about this with my partner, Chris. He knew how I felt about her and he was open, he was like, “Okay, you know, we’re in a polyamorous relationship. What would that be like [if] if you had a partnership with her and with me?” And it just filled me with such joy to think about it and to allow that to be a possibility. 

She and I didn’t even get to that conversation. She just shut it down. 

August (narration):

Still, Judy said she gained something important from the experience, beyond what’s possible with sex with a fellow woman…and beyond her fisting first. 

Judy:  

What I really gained from that experience is, you walk away with your pleasure. You are intact. Like, me loving me, is making sure that I take stock of my part of it, right? And my heart, my pussy, my spiritual experience, they’re intact, they’re intact. And they’re mine. I get to walk away with all of it. 

August (narration):

Yes, it was heartbreaking, at the end of the day. But that’s why Judy wrote “Cave Walls.”

Judy: 

I wrote this story to honor her and to honor that moment. And that transformation inside of me where my pleasure boundaries got blown out, and I discovered this whole new frontier. 

With the sort of devastating outcome of that night was for me to say, 

…what if it was just that and I can walk away with it and hold it dear? I didn’t ever intend to write about it. But that’s what happened. And it’s mine. It – The story’s mine. And I cherish it.

[acoustic chord riff]

August (narration):

Find both stories that inspired today’s episode, “My First Shared Orgasm,”by Suzannah Weiss and “Cave Walls,” by Judy Calabrese, in The Big Book of Orgasms, Volume 2, most anywhere books are sold—or click the direct link in the show notes.

You can also follow Suzanna on Twitter: @suzannahweiss, and Instagram: @weisssuzanna, and find information on courses she’s teaching about female pleasure—including Orgasm Cure, for people with a vulva—at suzannahweiss.com. 

For more from Judy Calabrese, visit judycalabrese.com and check out her erotica storytelling show, Litherotica. Subscribe on YouTube to see a recent live stream. And if you have a story you’d like to share with Judy, drop her a note at litherotica [at] gmail.com.

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And for more Girl Boner fun, check out my books – including Girl Boner, Girl Boner Journal and With Pleasure, co-written by sex therapist Jamila M. Dawson, at augustmclaughlin.com or the link in the show notes.

Thanks so much for listening.

[outro music that makes you wanna dance!]