True Sex: A Very Happy Ending
What was your upbringing like, and how did it color your approach to sex and relationships?
I am extremely lucky to come from a supportive family and had a healthy, happy childhood. My parents have been happily and monogamously married for 34 years. I was always taught that I should do whatever makes me happy and was never under any pressure to date or not date, etc. We are Jewish, but not at all religious. So I had a clean slate, which I guess is a boring start. I was pretty nerdy in high school and didn’t even kiss a boy until I was 18 and drunk at a New Year’s party. Then I went to college and basically tried everything I could (haha). Having an open and supportive upbringing made me feel like I could do anything I wanted in regards to sex or relationships, knowing that I had a support circle behind me no matter what.
Did you purposely wait until college to begin experimenting, or did your urges just naturally develop on that timetable?
I think it was honestly a bit of both. I went to high school in a small town and was definitely not one of the popular kids. I had a close group of single girlfriends and just never really met any boys – but I wasn’t particularly antsy to. I started drinking and masturbating the summer before college because I wanted to “grow up” a bit. But then the sex gods spited me and I got sorted into an all-girls dormitory. I think moving out and going to college helped my self-esteem a lot, and then once I moved out of the dorm I finally started meeting guys and experimenting.
Beyond the New Year’s kiss, what was your first full-on experience?
I had a couple male buddies from an old summer job: two of them were supposed to come up for the weekend and visit me at school. At the last minute, one of them mysteriously dropped out. So it was down to just this one guy coming to visit me for an entire weekend. Neither of us had ever done anything beyond kissing before. I was a bit nervous to hook up with him, but we finally went for it and it was nice because I already had a friendship with this guy. We fooled around and both gave/received oral for the first time, which was wild! Even though we didn’t have penetrative sex I still often think of that time when I think of losing my virginity, because it was my first time being naked and vulnerable with someone.
How did your sex life develop from there?
From there I kind of ended up in a weird “friends with benefits” (FWB) type situation with that guy. Looking back it was not a healthy relationship at all and it essentially ruined our friendship. He was extremely hot and cold.
Were you frustrated being seemingly unable to “go all the way” after so many false starts?
Very. Practically all my experiences were with men who were unavailable emotionally, or too involved with my friend circles to want to have sex. There’s this weird stigma that fooling around is totally fine but penetrative sex is like, the be all and end all, which I totally disagree with. At the time I found it very frustrating because I don’t think penetration makes a sexual encounter any more meaningful, as long as it’s safe – and I was very self-conscious that no one wanted to fuck me. I felt like I was only good for giving blowjobs.
How did you muster the courage to go the male masseuse route, and how did you arrange it?
My FWB was actually the one who inspired me to seek out the masseuse. I told him I loved the idea of a happy ending massage and he was all, “You would never actually do that.” Did you know finding a happy ending massage parlor, as a single woman, is incredibly difficult? The shadier “rub and tug” places cater to men, and the nicer “erotic fantasy spas” cater to single men or couples! I spent a long time doing extensive Google/Craigslist searches until I finally came across a winner. He’s an RMT operating out of his apartment and his website lists “tantric massage.” Of course it doesn’t say anything explicitly on the website because of legal concerns, but enough was implied for me to understand. We set up an appointment and I took the bus to his place! I was a nervous wreck.
Did you know going in that you planned to officially lose your virginity that day?
Actually I didn’t have that planned at all! I honestly thought it would be a massage with some fingering and nipple play type thing. Basically, how it went down was I got to his place and we sat on the couch and just chatted for a while. He was very respectful and charming. He asked me about why I was there and what I wanted. He offered me the basic (aka non sexual) service or the “we’ll see what happens” service, which entailed him going beyond a basic massage only as far and as long as I was comfortable. So we get into it and it was all based on my encouragement. He fingered me and it felt great. He was noticeably hard and I was enjoying things so I encouraged him to continue. I asked him to kiss my neck (because that’s my weakness), and it escalated (all with my consent) to him getting on top of the massage table with me and we had sex. I was blown away! Afterwards, I made a joke that he must love his job and he told me that he never sleeps with clients. He told me I was the exception (I don’t know if I actually believe this or not but it seemed fairly genuine). I never told him it was my first time.
Following these experiences, how did your tastes change – for instance, experimenting with women, multiple partners and the like?
Well, my FWB taught me everything I didn’t want in a partner. I knew that I needed a partner that was more experienced than me, and who could introduce me to new experiences. So I joined OKCupid and met an incredible guy just over a year ago. He taught me all about open relationships, polyamory and kink, and helped shape my views/tastes.
It almost seems he’s as much a mentor as a lover.
He was in an open relationship with another girl at the time and was trying to meet new partners and eventually set up a threesome. So he messaged me and we hit it off. We met for a date at the local coffee shop and talked for a long time about open relationships and being polyamorous.
Describe for us the threesome with your OKCupid hookup.
So I’d been hooking up with the guy for a couple months and then I met his girlfriend. She was nice, and they were both really interested in having a threesome, so a few weeks later we set a date and I met them at her place. We all got into her bed and started watching Superbad – it was very awkward. They started kissing and then we got into things a bit. She was very shy and I clearly am not, so a lot of the attention was on me. She watched him fuck me, we cuddled and I touched her a bit. She went down on me, which was unreal – but she got really overwhelmed, I think. It was both of our first times experimenting with another woman. But I found out after that she had really been thinking she was attracted to women for a long time. Not too long after our threesome she started dating another woman and broke up with OKCupid Guy to be just with her. Things got pretty awkward between her and I after that. She unfortunately works at my local frozen yogurt place, so now, every time I go to get a tasty treat I get served by the girl who tasted my treat (hahaha)!
Too funny! In summary, what would you like to achieve in your relationships going forward? How serious would you like to get?
I think the main thing right now is having a partner/partners who are on the same page as me. I’m 21 fucking years old and have a solid decade ahead of me before I even want to consider the idea of marriage! I’m looking for people who share the same values and preferences as me regarding sex and relationships – respecting each other, an open mind and willingness to try new things, and mutual trust. They have to care about my needs and pleasure, but also be willing to give me space. I would maybe like to be in an open relationship – where I have a primary partner or significant other – as that’s something I’ve never set a label on in the past. Someday I would like to have a traditional family, with a husband and kids. But I think even when I’m married I would want to have a slightly open marriage: I don’t really believe that one person can fully satisfy someone’s emotional and physical needs. 
