sex diaries

The Non-Monogamous Actor in a Very Hot Relationship on Vacation

Once a week, Daily Intel peeks behind doors left slightly ajar. This week, the Non-Monogamous Actor in a Very Hot Relationship on Vacation: male, 39, straight, Williamsburg, in a wide-open relationship.

8:40 a.m. Wake up next to Maryann, warm, half-asleep, cuddling. Seven days into my trip, having fled New York after not seeing her for a month. Seven days of hot sex so far, and a week yet to go.
8:50 a.m. Occurs to me that this is more sex than I’ve had in three years. Maryann is the third person I’ve slept with since ending a (mostly) celibate two years, preceded by an addled series of random hook-ups, preceded by the brutal, slow death of a three-year monogamous relationship, preceded by a decade-long (mostly) monogamous relationship.

9 a.m. Maryann slides back into bed, pressing her body against mine. I’m already aroused, and her hands on my body quickly have me hard. She slips off her nightgown and kisses down my chest, my belly, then lower down. I am aware, again, that her skills at giving head have improved considerably since I met her, and since her recent “playdates” with experienced teachers. We finish with slow, gentle sex, wake-up sex that leaves us with a glow. She leaves for work, I set off to bike around a new city.
3:10 p.m. Back from biking around, intend to work. Instead sleepy, flipping through “Yoni Massage.” I’m interested in learning about sexuality in all (well, most) of its possibilities, though this was inspired by Maryann telling me about a play-partner experience. Reading quickly fills my mind with elaborate fantasy; I masturbate.
4:20 p.m. I awake to find, to my surprise, that I’m aroused. Am I oversexed? Is there such a thing? I run my fingers along myself, around in circles just above my pubic bone, over my nipples. I’m fully hard again but don’t want to be exhausted for Maryann. My resolve crumbles immediately. I finish loudly, wonder if any roommates are around to hear me, and fall asleep.
9 p.m. At dinner with my high-school best friend and girlfriend, whom I haven’t seen in years. They found themselves in the same city with respective kids. It is so utterly fitting that they found each other. Their relationship is new, hot, and beautiful.
11:10 p.m. Maryann left early and is asleep. Sarah was the first one to really blow my mind sexually, the first one to break my heart with her meaningless hook-ups, and the first one to be heartbroken by my possibly-more-than-meaningless sex with others. Now I can see her as someone who helped set the course of my sexuality, someone who is still smoking hot, with that wildness in her eyes that first made me dizzy with desire.
11:45 p.m. Maryann is not asleep. It appears that erotic, sexual energy isn’t a finite resource that gets used up like a bottle of water, but it rather increases with frequency of its use. We had sex in simple missionary that was sweet and gentle, not mind-blowing, but just, well, really nice.

9 a.m. Maryann’s at work. We met seven months ago and have built a connection based on strong sexual desire and interest in exploring new things. That quickly involved other interests, since I couldn’t have sex with someone for more than a week if there was nothing to talk about afterward. I have a deep, abiding interest in having lots of sex with multiple partners in a consensual, respectful, healthy way, if such a thing is possible for me to learn. And Maryann wants something similar. Which is why this is working.
10 a.m. Although it isn’t without rough patches. I feel jealous today. Not the old kind of jealous, that she is with someone else, but the new kind of jealous, that I’m happy for her that she’s finding these new experiences and I’m jealous that I’m not.
1:20 p.m. Biking around to find massage oil. Can’t believe I’ve been here a week and no massage has been given or received! Other priorities.
2:30 p.m. Massage oil. Check.
3:30 p.m. Suddenly overwhelmed that I’ve not had any other sex partners since meeting Maryann. Ah, well, except for Carin. But we didn’t really have sex. I catch myself doing the same definition game that annoyed me when Maryann did it. It is sex when Maryann and a playdate get each other off, and it was sex when Carin and I did the same just before I left New York.
5:45 p.m. Visiting Sarah with her kids. Sarah walks me out to the gate as I leave, her eyes smoldering. My desire for her is fully reawakened, white-hot, and unspoken, as it must be.
6:10 p.m. Thinking about Sarah and my high-school best friend being together, and my moment of piercing desire for her as I was leaving.
7 p.m. Dinner with Maryann. A long “What are we doing?” discussion. To summarize: She feels that her sex play with others is technical, and my interest in sex with people is emotional, and there is a distance and a disconnect between those interests. But we’re also both new at this. We decide to let it ride and see what happens.
8 p.m. She tells me that after our first long sex weekend, it was my tearjerker of a speech laying out my plans to be callous and slutty (I was trying to create some distance between us) that set her off to explore the world of sex play, non-monogamy, and polyamory. I point out that she had already done all the prep.
10:45 p.m. Sex. Maryann on top, rides us both to orgasm. Mmmmmm.

5:30 p.m. Maryann back from work early, with a fire to have sex. We did, from behind. “Hard,” she said. “Harder.” And I complied — despite the fact that she had some pain. Hurts so good.
8:20 p.m. Live music. A friend of Maryann’s is dating the guitarist. She’s an artist and hot. I’m attracted to her and have fantasies of Maryann and her hooking up. Although Maryann has never expressed interest in women, a bit disappointing.
11:10 p.m. Okay. Rather intense. Maryann is crying, concerned that she has contracted herpes from me, that this is the cause of the pain. Although I don’t have outbreaks, I know I could spread it. We have very safe sex, but still there are risks. I contracted it from a woman I spent three years with. I have an itching desire to post something to, like, “Thank you, I’ll always have something to remember you by,” or to say to her now husband, “We have a lot in common.” But, no, there is no real point to that. When we act in resentment, we pick up hot coals, and the first one to burn is ourselves.
11:20 p.m. Online research. Maryann is in pain. A Google image search of herpes is not a fun time.
11:40 p.m. I examine with a flashlight. It’s not herpes. Torn perineum. The skin at the base of her vagina has been split, and it is sore and angry.
11: 50 p.m. Exhausted. Convince Maryann to go to OB/GYN tomorrow, before we leave for a road trip to my family’s. Despite everything, I get her off with a vibrator, focusing on her clitoris.

9:30 a.m. Wanted to be on the road by 10 a.m. Not gonna happen. Maryann is at the doctor’s.
3:30 p.m. On the road, discussing boundaries and intentions for a Saturday sex party. Maryann is menstruating in addition to a torn perineum. But she is making arrangements to be able to handle the sex party. In particular, using a diaphragm and numbing cream the doc gave her.
9 p.m. At a B&B. I point out that I would prefer my bookish cousins not come along with us to the kinky sex party. She agrees.
11:45 p.m. We’re humping each other, hard. Suddenly, we’re almost having anal sex. “Is it now that you want to try it?” she asks. Well, no. Not now. Orgasm.

9:40 a.m. I woke up to a beautiful woman going down on me. This is a wonderful way to start the day. And then she rolled over and offered up her ass. And I fucked her. It was so intense and hot we both orgasmed within 60 seconds.
9:45 a.m. And then she, menstruating, torn perineum and all, asked that I step outside while she cleaned up. Here I am, outside. Am I hurting her? But she wants it. Confused.
6:20 p.m. Family dinner. Everyone is enamored with Maryann. I see her beauty through others’ eyes.
11:30 p.m. More sex-party talk. We agree that we’ll have sex with just each other and then talk about how we feel. I’m feeling vulnerable. Raw. I’ve never done this before. Neither has she.

Noon Museum with my mom. Seeing floral paintings of vulvas.
4 p.m. Outside a really good leather-and-toys shop. I am interested in the books on ropes and bondage, mostly because I’m interested in sailing, but also because the women I’ve been with have expressed an interest in being dominated. So I should learn how to do that.
10 p.m. At a house party. Maryann and her friend spend 90 minutes getting ready for the sex party. Maryann’s in black heels, fishnets, a thin and very short pink top, and a fluffy hat. That’s it.
12:15 a.m. The party is interesting. A dance room and a lounging room, and a bunch of rooms of various sizes and lighting with beds and pillows and mattresses. Don’t like the music, but we dance anyway.
1:20 a.m. Maryann leads me to a couple rooms and finally picks one she’s comfortable in. There are five other couples anchored by a blonde and a frat boy who have been having sex for an hour straight. Wonder what they’re on.
1:30 a.m. I can’t concentrate. I feel like people are sticking their heads in the door and watching me. I’ve never done this before. Maryann goes down on me. Right as I feel myself getting hard, I see a friend I consider a sister bounce into the room. Lose erection immediately. Crap.
2 a.m. Wow. Took Maryann from behind as five other couples did the same. Suddenly the whole room was in the same position. Hot. We were next to another couple that kept brushing us. The skin-to-skin contact was definitely a turn-on.
5 a.m. Drive home. Wow. What a night. Maryann made out with a woman we had sex next to, and I made out with a woman who watched us, who thought I was hot. It was all-around safe and sexy and good.

8 p.m. Spend the day alternately with my family and rehashing the night before.
11 p.m. Maryann’s leaving tomorrow. We spend the last night, as she calls it, “practicing our asexuality.” Which lasted for four minutes. When our bodies fit together and the sexual energy started to flow, she went down on me. And I wanted to make her orgasm, and she wanted to, so I did.

TOTALS: Five acts of intercourse, one public; one act of orgasmic humping; one act of anal sex; two acts of vibrator petting; four acts of fellatio; two acts of masturbation; one torn perineum.

The Non-Monogamous Actor in a Very Hot Relationship on Vacation